Benzamide → HCID 67250615, compound

HRID 2039742Notes

Reaction equation

[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].[NH2:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[C:19]3[C:26]([C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:28])=[CH:25][NH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:13]=[C:14]([Cl:16])[CH:15]=1.C(N)(=O)C1C=CC=CC=1>>[C:1]([NH:4][CH2:5][C:6]([NH:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([NH:17][C:18]2[C:19]3[C:26]([C:27](=[O:28])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:25][NH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:11]=1)=[O:8])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 2331Benzamide

HCID 10972Acetylglycine

HCID 58327724HCID 58327724, compound

Product 1

HCID 67250615HCID 67250615, compound

Procedure

2-Acetamido-N-(3-((5-benzoyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-5-chlorophenyl)acetamide was synthesized using 2-acetamidoacetic acid and (4-((3-amino-5-chlorophenyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(phenyl)methanone according to the procedure for the synthesis of N-3-((5-benzoyl-7H-pyrrolo[2,3-d]pyridine-4-yl)amino)phenyl)benzamide. A white solid was obtained. M.p.>300° C.; 400 MHz 1HNMR (DMSO-d6) δ 11.53 (s, 1H), 10.24 (s, 1H), 8.53 (s, 1H), 8.25-8.22 (m, 1H), 8.11-8.10 (m, 1H), 8.00 (d, J=2.0 Hz, 1H), 7.87 (s, 1H), 7.86-7.85 (m, 1H), 7.81-7.81 (m, 1H), 7.69-7.67 (m, 1H), 7.61-7.57 (m, 2H), 7.51-7.50 (m, 1H), 3.87 (d, J=6.0 Hz, 2H), 1.90 (s, 3H); LCMS [M+H] 463.

Workup

customA white solid was obtained

Sources & evidence

ORD record: ord-4ab133081d46467aa658fff598a9ba17
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580803B2

Reaction notes

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