4-(Chloromethyl)benzonitrile → HCID 25096447, compound

HRID 2067557Notes

Reaction equation

HRID 2067557 reaction equation
ClCC1C=CC(C#N)=CC=1.Br[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([N:38]2[CH2:42][CH2:41][NH:40][C:39]2=[O:43])=[N:35][C:34]=1[CH3:44])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[NH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([CH2:13][CH2:12][N:40]2[CH2:41][CH2:42][N:38]([C:36]3[S:37][C:33]([C:31]([NH:30][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:32])=[C:34]([CH3:44])[N:35]=3)[C:39]2=[O:43])=[CH:15]1

Participants

4

Reactant 3

HCID 701274-(Chloromethyl)benzonitrileHCID 769243-(2-Bromoethyl)indoleHCID 59481185N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 25096447HCID 25096447, compoundYield 22%

Procedure

Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with 3-(2-bromoethyl)-1H-indole to react with N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 22% yield: mp 215-217° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 10.86 (s, 1H), 8.50 (t, J=6.0 Hz, 1H), 7.57 (d, J=6.0 Hz, 1H), 7.36-7.20 (m, 7H), 7.10-6.96 (m, 2H), 4.38 (d, J=6.0 Hz, 2H), 3.96 (t, J=9.0 Hz, 2H), 3.61-3.51 (m, 4H), 2.95 (t, J=9.0 Hz, 2H), 2.47 (s, 3H); MS (ES+) m/z 460.2 (M+1).

Sources & evidence

ORD record
ord-0b8874505a4940f680b9737c06d3be17
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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