4-(dimethylamino)-2-Butynoic acid synthesis
- Product Name:4-(dimethylamino)-2-Butynoic acid
- CAS Number:118764-05-9
- Molecular formula:C6H9NO2
- Molecular Weight:127.14
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Yield:118764-05-9 56%
Reaction Conditions:
Stage #1: N,N-Dimethylpropargylaminwith n-butyllithium in tetrahydrofuran at -78; for 0.5 h;
Stage #2: carbon dioxide in tetrahydrofuran at 20; for 1 h;
Stage #3: with hydrogenchloride;water monomer in tetrahydrofuran; pH=3 - 4;
Steps:
112.1
Example 112: Preparation of fZ>l-(3-(4-(3-chloro-2,4-difluorophenylamino)- 7-methoxyquinazolin-6-yloxy)azetidin-l-yl)-4-(dimethylamino)but-2-en-l- one; Step 1) 4-(dimethylamino)but-2-inoic acid; 3.0 ml of 3-dimethylamino-l-propyne was diluted with 30 mi of tetrahydrofuran, and 27 mi of a 1.6M n-butyl lithium-containing tetrahydrofuran solution was gradually dropwise added thereto at -78 °C . The resulting mixture was stirred at -78 °C for 30 minutes and heated to room temperature while bubbling with CO2 gas for one hour. After the reaction terminated, the resulting solution was acidified to pH 3-4 with a 35% HCl, distilled under a reduced pressure and dried in vacuum. The resulting residue was dissolved in hot ethanol, and the resulting solution was stirred at 0°C . The resulting solid was filtered under a reduced pressure to obtain the title compound (2 g, 56%) in a crystal form.1H-NMR (300MHz, D2O) δ 4.07 (s, 2H), 2.89 (s, 6H).
References:
WO2008/150118,2008,A2 Location in patent:Page/Page column 64-65
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