CB5083 synthesis

10synthesis methods

Product Name:CB5083
CAS Number:1542705-92-9
Molecular formula:C24H23N5O2
Molecular Weight:413.47

1-(4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl)-2-methyl-1H-indole-4-carbonitrile

1542705-83-8

1542705-92-9

Compound 7 (CAS:1542705-83-8, 180 mg, 0.46 mmol) was used as a raw material and dissolved in a mixed solvent of ethanol (8 mL) and water (1 mL). Palladium acetate (Pd(OAc)2, 11 mg, 0.046 mmol), triphenylphosphine (PPh3, 14 mg, 0.053 mmol), and acetaldehyde oxime (53 mg, 0.92 mmol) were then added sequentially. The reaction mixture was heated to reflux for 2 hours. After completion of the reaction, the mixture was concentrated and the residue was purified by fast column chromatography (silica gel as stationary phase and dichloromethane/methanol=20:1 as eluent) to afford the target product 1-(4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl)-2-methyl-1H-indole-4-carboxamide (II, 110 mg, Yield 58%). Mass spectrometry (LRMS) analysis of the product showed that the calculated value of (M+H)+ m/z was 414.19 and the measured value was 414.20. Nuclear magnetic resonance hydrogen spectrometry (1H-NMR, 300 MHz, D3COD) data were as follows: δ 7.72 (d, 1H), 7.44 (d, 1H), 7.41 (m, 1H), 7.31 (m, 3H), 7.25 (m, 1H), 6.96 (t, 1H), 6.77 (s, 1H), 4.71 (d, 2H), 4.63 (s, 1H), 4.05 (t, 2H), 2.11 (t, 2H), 2.45 (s, 3H).

1542705-83-8
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1542705-92-9
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Yield: 70%

Reaction Conditions:

with Acetaldehyde oxime;palladium diacetate;triphenylphosphine in ethanol;water at 90; for 2 h;Inert atmosphere;

Steps:

5 4.2.5 1-(4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl)-2-methyl-1H-indole-4-carboxamide (CB-5083)
General procedure: At room temperature, to the solution of the 16 (262mg, 0.663mmol) in ethanol (12mL) was added PPh₃ (34mg, 0.13mmol), Pd(OAc)₂ (29.2mg, 0.13mmol), acetaldehyde oxime (35.4mg, 0.60mmol) and water (1.5mL). The resulting mixture was refluxed for 2h, cooled down to room temperature and concentrated in vacuo. The residue was purified by flash chromatography (petroleum ether/EtOAc=2:1) to afford CB-5083 (191mg, yield 70%, purity 99%).

References:

Wang, Xueyuan;Bai, Enhe;Zhou, Hui;Sha, Sijia;Miao, Hang;Qin, Yanru;Liu, Zhaogang;Wang, Jia;Zhang, Haoyang;Lei, Meng;Liu, Jia;Hai, Ou;Zhu, Yongqiang [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 3,p. 533 - 544]

7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2,4-diol

1478126-83-8
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References

2,4-Dichloro-7,8-dihydro-5H-pyrano[4,3-d]pyriMidine

944902-88-9
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1542705-92-9
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References

29943-42-8 Synthesis

29943-42-8
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1542705-92-9
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References

Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate

127956-11-0
107 suppliers
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1542705-92-9
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References