Triethylamine → 2-(Dimethylamino)-N-(5-(3,5-dimethylisoxazol-4-yl)-2-oxo-3-phenylindolin-3-yl)acetamide
Reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][C:5](O)=[O:6].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[NH2:40][C:41]1([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:49]2[C:44](=[CH:45][CH:46]=[C:47]([C:50]3[C:51]([CH3:56])=[N:52][O:53][C:54]=3[CH3:55])[CH:48]=2)[NH:43][C:42]1=[O:57]>C(Cl)Cl.O>[CH3:2][N:3]([CH3:8])[CH2:4][C:5]([NH:40][C:41]1([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:49]2[C:44](=[CH:45][CH:46]=[C:47]([C:50]3[C:51]([CH3:56])=[N:52][O:53][C:54]=3[CH3:55])[CH:48]=2)[NH:43][C:42]1=[O:57])=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 2-(dimethylamino)acetic acid hydrochloride (87 mg, 0.62 mmol), HATU (118 mg, 0.31 mmol), and Et3N (94 mg, 0.93 mmol) in CH2Cl2 (10 mL) was stirred at RT for 0.5 hours, and then 3-amino-5-(3,5-dimethylisoxazol-4-yl)-3-phenylindolin-2-one (100 mg, 0.31 mmol) was added and the mixture was stirred for another 12 h. And water (10 mL) was added, the mixture was extracted with CH2Cl2 (2×20 mL), combined organic phase, washed with brine (20 mL), dried with Na2SO4, concerned in vacuo, the mixture was purified with column chromatography to give product (50 mg, 40%) as a solid. 1H NMR (400 MHz, DMSO-d6): δH 10.70 (s, 1H), 9.74 (s, 1H), 7.26-7.40 (m, 7H), 6.99 (d, J=8.0 Hz, 1H), 4.07 (d, J=16.0 Hz, 1H), 3.93 (d, J=16.0 Hz, 1H), 2.78 (s, 3H), 2.71 (s, 3H), 2.38 (s, 3H), 2.20 (s, 3H). MS (ESI) m/e [M+1]+ 405.
Workup
- stirringthe mixture was stirred for another 12 h
- extractionthe mixture was extracted with CH2Cl2 (2×20 mL)
- washwashed with brine (20 mL)
- dry with materialdried with Na2SO4
- customthe mixture was purified with column chromatography
Sources & evidence
- ORD record
- ord-e542b75dbdae4212a27555eadc5d9f56
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09393232B2
Reaction notes
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