4-(Chloromethyl)benzonitrile → HCID 25096445, compound

HRID 2067556Notes

Reaction equation

HRID 2067556 reaction equation
ClCC1C=CC(C#N)=CC=1.Br[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1.[CH2:19]([NH:26][C:27]([C:29]1[S:33][C:32]([N:34]2[CH2:38][CH2:37][NH:36][C:35]2=[O:39])=[N:31][C:30]=1[CH3:40])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([NH:26][C:27]([C:29]1[S:33][C:32]([N:34]2[CH2:38][CH2:37][N:36]([CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[C:35]2=[O:39])=[N:31][C:30]=1[CH3:40])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 701274-(Chloromethyl)benzonitrileHCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 59481185N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 25096445HCID 25096445, compoundYield 27%

Procedure

Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with 2-(bromomethyl)tetrahydro-2H-pyran 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 27% yield: 1H NMR (300 MHz, CDCl3) δ 7.34-7.30 (m, 5H), 5.86 (s, 1H), 4.56 (d, J=3.0 Hz, 2H), 4.08 (t, J=9.0 Hz, 2H), 3.98-3.94 (m, 1H), 3.84-3.3.63 (m, 2H), 3.55-3.35 (m, 3H), 3.18-3.16 (m, 1H), 2.62 (s, 3H), 1.86-1.83 (m, 1H), 1.60-1.22 (m, 5H); MS (ES+) m/z 415.3 (M+1).

Sources & evidence

ORD record
ord-050885e124b84039b9379bf1d1f0a35a
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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