Aniline → HCID 11718558, compound

HRID 2067268Notes

Reaction equation

HRID 2067268 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=CC(C(C2C=C(N3C=C(CCO)N=N3)C=CC=2C)=O)=C(C)C=1.NC1C=CC=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]([C:16]([C:13]3[CH:14]=[CH:15][C:10]([NH:9][C:3]4[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=4)=[CH:11][C:12]=3[CH3:33])=[O:17])[CH:23]=2)[CH:28]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 11510648HCID 11510648, compoundHCID 68418335HCID 68418335, compound

Product 1

HCID 11718558HCID 11718558, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and aniline (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 197.0, 147.9, 146.3, 143.4, 142.5, 140.4, 137.0, 135.5, 134.6, 132.2, 129.5, 127.6, 123.5, 121.4, 121.0, 119.9, 118.1, 111.4, 61.6, 28.7, 22.3, 19.5

Workup

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

Sources & evidence

ORD record
ord-6b1e6d405d384c61be7a7ba55072275c
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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