3'-Aminoacetophenone → HCID 11626640, compound

HRID 2067269Notes

Reaction equation

HRID 2067269 reaction equation
F[C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[C:22]([N:24]3[CH:28]=[C:27]([CH2:29][CH2:30][OH:31])[N:26]=[N:25]3)[CH:21]=[CH:20][C:19]=2[CH3:32])=[O:17])=[C:12]([CH3:33])[CH:11]=1.BrC1C=C[C:38]([C:41](C2C=C(N3C=C(CCO)N=N3)C=CC=2C)=[O:42])=C(C)C=1.NC1C=C(C(=O)C)C=CC=1>>[OH:31][CH2:30][CH2:29][C:27]1[N:26]=[N:25][N:24]([C:22]2[CH:21]=[CH:20][C:19]([CH3:32])=[C:18]([CH:23]=2)[C:16]([C:13]2[CH:14]=[CH:15][C:10]([NH:9][C:3]3[CH:4]=[C:5]([C:41](=[O:42])[CH3:38])[CH:6]=[CH:7][CH:2]=3)=[CH:11][C:12]=2[CH3:33])=[O:17])[CH:28]=1

Participants

4

Reactant 3

HCID 74173'-AminoacetophenoneHCID 11510648HCID 11510648, compoundHCID 68418335HCID 68418335, compound

Product 1

HCID 11626640HCID 11626640, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and 1-(3-amino-phenyl)-ethanone (0.13 mmol). The crude product was purified by continuous gradient flash chromatography using MeOH/DCM/petroleum ether (40-60) 0:50:50, 0:100:0 and 5:95:0 as the eluent to afford the title compound as yellow solid. 13C NMR (CDCl3) δ 197.8, 197.1, 147.1, 146.3, 143.3, 142.3, 141.2, 138.5, 137.1, 135.3, 134.7, 132.3, 129.8, 128.5, 124.8, 123.2, 121.5, 120.0, 119.9, 119.6, 118.7, 111.8, 61.6, 28.7, 26.7, 22.2, 19.6

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-b17a55dfe9b54060b909cca1d944873f
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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