3-Aminobenzonitrile → HCID 11618997, compound

HRID 2067270Notes

Reaction equation

HRID 2067270 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.[NH2:59][C:60]1[CH:61]=[C:62]([CH:65]=[CH:66][CH:67]=1)[C:63]#[N:64]>>[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]([CH:48]=2)[C:41]([C:38]2[CH:39]=[CH:40][C:35]([NH:59][C:60]3[CH:61]=[C:62]([CH:65]=[CH:66][CH:67]=3)[C:63]#[N:64])=[CH:36][C:37]=2[CH3:58])=[O:42])[CH:53]=1

Participants

4

Reactant 3

HCID 167023-AminobenzonitrileHCID 11510648HCID 11510648, compoundHCID 68418335HCID 68418335, compound

Product 1

HCID 11618997HCID 11618997, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and 3-amino-benzonitrile (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, 146.5, 145.7, 142.4, 142.1, 142.1, 135.4, 135.0, 134.5, 132.2, 130.7, 127.7, 124.9, 123.3, 121.1, 120.7, 120.6, 118.8, 118.6, 118.5, 112.2, 60.2, 29.2, 21.9, 18.9

Workup

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

Sources & evidence

ORD record
ord-355110d9013f431184421e402c0e01b4
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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