3,4-Dimethylaniline → HCID 11503085, compound

HRID 2067273Notes

Reaction equation

FC1C=C(F)C=CC=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](C2C=C(N3C=C(CCO)N=N3)C=CC=2C)=O)=[C:12]([CH3:33])[CH:11]=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.CC1C=C(N)C=CC=1C>>[CH3:33][C:12]1[CH:11]=[C:10]([NH:9][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:15]=[CH:14][C:13]=1[CH3:16]

Participants

Reactant 3

HCID 72483,4-Dimethylaniline

HCID 11510648HCID 11510648, compound

HCID 68418335HCID 68418335, compound

Product 1

HCID 11503085HCID 11503085, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and 3,4-dimethyl-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 (DMSO-d6) δ 196.0, 148.9, 145.7, 142.7, 142.3, 138.4, 137.1, 135.5, 135.1, 134.4, 132.0, 130.5, 130.2, 125.4, 121.9, 120.7, 120.2, 118.2, 118.0, 117.0, 110.4, 60.2, 29.2, 22.2, 19.5, 18.8, 18.7

Workup

customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-fbcf93d9339d4923986015a505a04764
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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