m-Aminoacetanilide → HCID 11554573, compound

HRID 2067276Notes

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=C([NH:66][C:67](=[O:69])[CH3:68])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]([NH:66][C:67](=[O:69])[CH3:68])[CH:6]=[CH:7][CH:2]=3)=[CH:11][C:12]=2[CH3:33])=[O:17])[CH:28]=1

Participants

Reactant 3

HCID 7604m-Aminoacetanilide

HCID 11510648HCID 11510648, compound

HCID 68418335HCID 68418335, compound

Product 1

HCID 11554573HCID 11554573, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and N-(3-amino-phenyl)-acetamide (0.13 mmol). The crude product was purified by continuous gradient flash chromatography using NH3(aq.)/MeOH/DCM 0:0:100, 1:9:90 as the eluent to afford the title compound as yellow solid. 13C NMR (DMSO-d6) δ 196.1, 168.2, 147.9, 145.6, 142.4, 142.0, 141.2, 140.1, 135.1, 135.0, 134.3, 131.9, 129.3, 126.0, 120.6, 120.2, 118.2, 117.6, 114.2, 112.7, 111.1, 110.0, 60.1, 29.1, 24.0, 22.1, 18.7

Workup

customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-2006465bc1874a7ca46cb5f5fc17c432
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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