3-(Trifluoromethyl)aniline → HCID 11496666, compound

HRID 2067271Notes

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.[F:59][C:60]([F:69])([F:68])[C:61]1[CH:62]=[C:63]([NH2:67])[CH:64]=[CH:65][CH:66]=1>>[OH:56][CH2:55][CH2:54][C:52]1[N:51]=[N:50][N:49]([C:47]2[CH:46]=[CH:45][C:44]([CH3:57])=[C:43]([C:41]([C:38]3[CH:39]=[CH:40][C:35]([NH:67][C:63]4[CH:64]=[CH:65][CH:66]=[C:61]([C:60]([F:59])([F:68])[F:69])[CH:62]=4)=[CH:36][C:37]=3[CH3:58])=[O:42])[CH:48]=2)[CH:53]=1

Participants

Reactant 3

HCID 73753-(Trifluoromethyl)aniline

HCID 11510648HCID 11510648, compound

HCID 68418335HCID 68418335, compound

Product 1

HCID 11496666HCID 11496666, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and 3-trifluoromethyl-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 196.5, 146.8, 145.7, 142.3, 142.2, 142.1, 135.3, 135.1, 134.4, 132.2, 130.6, 130.2 (q), 127.6, 124.1 (q), 122.0, 120.7, 120.5, 118.5, 117.7 (q), 114.9 (q), 112.0, 60.2, 29.2, 21.9, 18.9

Workup

customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-55d741676d084bf5bdf8b887cdd58bb6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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