Water → 9-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid pyridin-3-ylamide

HRID 1710455Notes

Reaction equation

[O:1]=[C:2]1[C:7]2=[CH:8][C:9]3[C:14]([N:6]2[CH2:5][CH2:4][CH2:3]1)=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=3.CN(C(ON1N=[N:33][C:28]2[CH:29]=[CH:30][CH:31]=[N:32][C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C=CC=C(N)C=1.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[N:32]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:33][C:15]([C:12]2[CH:13]=[C:14]3[C:9]([CH:8]=[C:7]4[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][N:6]43)=[CH:10][CH:11]=2)=[O:17])[CH:27]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 9-oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid (983 mg, 4.29 mmol) in anhydrous DMF (5 mL) was added HATU (4.00 g, 10.5 mmol), DMAP (3.00 g, 25.0 mmol) and pyridine-3-ylamine (1.00 g, 10.6 mmol). The reaction was stirred at 65° C. for 36 h. The reaction was poured into water and the resulting precipitate was filtered, washed with water and triturated with cold MeCN to give the title compound (256 mg, 20%) as an analytically pure as a brown powder; ESI-MS m/z 306 [M+H]+.

Workup

filtrationthe resulting precipitate was filtered
washwashed with water
customtriturated with cold MeCN

Sources & evidence

ORD record: ord-2a40bde6bae84bda81a7ca3945110d31
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790712B2

Reaction notes

Loading…