3-Chloro-2-methylaniline → HCID 11597810, compound

HRID 2067274Notes

Reaction equation

FC1C=C(F)C=CC=1NC1C=CC(C(C2C=C(N3C=C(CCO)N=N3)C=CC=2C)=O)=C(C)C=1.Br[C:35]1[CH:40]=[CH:39][C:38]([C:41]([C:43]2[CH:48]=[C:47]([N:49]3[CH:53]=[C:52]([CH2:54][CH2:55][OH:56])[N:51]=[N:50]3)[CH:46]=[CH:45][C:44]=2[CH3:57])=[O:42])=[C:37]([CH3:58])[CH:36]=1.[Cl:59][C:60]1[C:61]([CH3:67])=[C:62]([NH2:66])[CH:63]=[CH:64][CH:65]=1>>[Cl:59][C:60]1[C:61]([CH3:67])=[C:62]([NH:66][C:35]2[CH:40]=[CH:39][C:38]([C:41]([C:43]3[CH:48]=[C:47]([N:49]4[CH:53]=[C:52]([CH2:54][CH2:55][OH:56])[N:51]=[N:50]4)[CH:46]=[CH:45][C:44]=3[CH3:57])=[O:42])=[C:37]([CH3:58])[CH:36]=2)[CH:63]=[CH:64][CH:65]=1

Participants

Reactant 3

HCID 68943-Chloro-2-methylaniline

HCID 11510648HCID 11510648, compound

HCID 68418335HCID 68418335, compound

Product 1

HCID 11597810HCID 11597810, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and 3-chloro-2-methyl-phenylamine (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, 148.6, 146.3, 143.5, 142.5, 139.9, 137.0, 135.7, 135.5, 134.6, 132.2, 130.9, 127.5, 127.1, 126.0, 122.4, 121.3, 119.9, 119.9, 117.8, 111.1, 61.6, 28.7, 22.3, 19.5, 15.0

Workup

customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-b17ec69d976a4e738f44c9a1e059afc6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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