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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List 2-[4-[3-[(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl]-1,2,4-oxadiazol-5-yl]pyrazol-1-yl]-N,N-dimethylacetamide
1360550-04-4

2-[4-[3-[(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl]-1,2,4-oxadiazol-5-yl]pyrazol-1-yl]-N,N-dimethylacetamide synthesis

7synthesis methods
1H-Pyrazole-1-acetamide, 4-[3-[1-[4-(2-amino-5-pyrimidinyl)phenyl]-1-cyclopropylethyl]-1,2,4-oxadiazol-5-yl]-N,N-dimethyl-

1360549-48-9
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(S)-BI 665915

1360550-05-5
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2-[4-[3-[(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl]-1,2,4-oxadiazol-5-yl]pyrazol-1-yl]-N,N-dimethylacetamide

1360550-04-4
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-

Yield:1360550-04-4 32 mg ，1360550-05-5 27 mg

Reaction Conditions:

with Chiralpak AD-H (available form Chiral Technologies, Inc., Exton, Pa.) semi-preparative (250×20 mm) HPLC column in ethanol;n-heptane;diethylamine;Resolution of racemate;

Steps:

Method 18 Synthesis of 2-[4-(3-{(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl}-1,2,4-oxadiazol-5-yl)-1H-pyrazol-1-yl]-N,N-dimethylacetamide (Example 115) and 2-[4-(3-{(1S)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl}-1,2,4-oxadiazol-5-yl)-1H-pyrazol-1-yl]-N,N-dimethylacetamide (Example 116, Table 1)

Enantiomers 115 and 116 are prepared by resolution of example 59 (100 mg) on a Chiralpak AD-H (available form Chiral Technologies, Inc., Exton, Pa.) semi-preparative (250×20 mm) HPLC column (eluting with 95% EtOH in heptane containing 0.1% diethylamine). The faster eluting enantiomer 115 having a retention time of 35 min and the slower eluting enantiomer 116 having a retention time of 73 min. The eluants are concentrated to provide Example 115 (32 mg) and Example 116 (27 mg

References:

US2013/195879,2013,A1 Location in patent:Paragraph 0421; 0422

2-(4-bromophenyl)-2-cyclopropylpropanenitrile

1360551-88-7
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2-[4-[3-[(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl]-1,2,4-oxadiazol-5-yl]pyrazol-1-yl]-N,N-dimethylacetamide

1360550-04-4
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References
Benzeneacetonitrile, 4-bromo-α-cyclopropyl-α-methyl-, (αR)-

1360551-90-1
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2-[4-[3-[(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl]-1,2,4-oxadiazol-5-yl]pyrazol-1-yl]-N,N-dimethylacetamide

1360550-04-4
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References
4-bromo-alpha-cyclopropyl-alpha-methylbenzyl alcohol

56041-75-9
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2-[4-[3-[(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl]-1,2,4-oxadiazol-5-yl]pyrazol-1-yl]-N,N-dimethylacetamide

1360550-04-4
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References
6952-89-2 Synthesis
(4-BROMOPHENYL)(CYCLOPROPYL)METHANONE

6952-89-2
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2-[4-[3-[(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl]-1,2,4-oxadiazol-5-yl]pyrazol-1-yl]-N,N-dimethylacetamide

1360550-04-4
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References