4-Fluorobenzylamine → HCID 59481208, compound

HRID 2067408Notes

Reaction equation

HRID 2067408 reaction equation
FC1C=CC(CN)=CC=1.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([F:19])[CH:18]=1)[CH2:14][NH2:15].[CH2:20]([N:27]1[CH2:31][CH2:30][N:29]([C:32]2[S:33][C:34]([C:38](O)=[O:39])=[C:35]([CH3:37])[N:36]=2)[C:28]1=[O:41])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([N:27]1[CH2:31][CH2:30][N:29]([C:32]2[S:33][C:34]([C:38]([NH:15][CH2:14][C:13]3[CH:12]=[C:11]([F:10])[CH:18]=[C:17]([F:19])[CH:16]=3)=[O:39])=[C:35]([CH3:37])[N:36]=2)[C:28]1=[O:41])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 1452113,5-DifluorobenzylamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 59481208HCID 59481208, compoundYield 45%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 3,5-difluorobenzylamine to react with 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white powder in 45% yield: mp 208-209° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.35-7.23 (m, 5H), 6.82 (s, 1H), 6.80 (s, 1H), 6.66 (t, J=8.7 Hz, 1H), 6.24 (t, J=5.7 Hz, 1H), 4.51 (d, J=5.7 Hz, 2H), 4.44 (s, 2H), 4.03 (t, J=8.4 Hz, 2H), 3.43 (t, J=8.4 Hz, 2H), 2.58 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 164.6, 162.6, 161.5, 161.4, 157.4, 155.3, 142.3, 135.4, 128.9, 128.2, 128.0, 116.7, 110.3, 102.8, 47.9, 43.0, 42.0, 41.6, 17.2; MS (ES+) m/z 443.2 (M+1).

Sources & evidence

ORD record
ord-d3653d9966644db9b1ef23cba2dcb6d3
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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