m-Aminoacetanilide → HCID 58327718, compound

HRID 2039748Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:13]1[C:14]2[C:21]([C:22]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)=[O:23])=[CH:20][NH:19][C:15]=2[N:16]=[CH:17][N:18]=1>>[C:24]1([C:22]([C:21]2[C:14]3[C:13]([NH:1][C:2]4[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=4)=[N:18][CH:17]=[N:16][C:15]=3[NH:19][CH:20]=2)=[O:23])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1

Participants

Reactant 2

HCID 7604m-Aminoacetanilide

HCID 86654848HCID 86654848, compound

Product 1

HCID 58327718HCID 58327718, compound

Procedure

N-(3-((5-(1-Naphthoyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)phenyl)acetamide was synthesized using N-(3-aminophenyl)acetamide and (4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(naphthalen-1-yl)methanone according to the general procedure A. A yellow solid was obtained. M.p.>300° C.; 400 MHz 1HNMR (DMSO-d6) δ 11.42 (s, 1H), 9.98 (s, 1H), 8.45 (s, 1H), 8.13 (d, J=8.4 Hz, 1H), 8.05-8.02 (m, 3H), 7.79-7.73 (m, 2H), 7.67 (s, 1H), 7.63-7.53 (m, 4H), 7.38-7.35 (m, 1H), 7.29-7.25 (m, 1H), 2.02 (s, 3H); LCMS [M+H] 422.

Workup

customA yellow solid was obtained

Sources & evidence

ORD record: ord-24e112fcba154a5fb24a00c2d38accf0
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580803B2

Reaction notes

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