4-Fluorobenzylamine → HCID 25094600, compound

HRID 560633

Reaction equation

HRID 560633 reaction equation
FC1C=CC(CN)=CC=1.[F:10][C:11]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:12]=1[CH2:13][NH2:14].[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:14][CH2:13][C:12]3[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:11]=3[F:10])=[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 1235892,5-DifluorobenzylamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 25094600HCID 25094600, compoundYield 76%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 2,5-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 76% yield: mp 176-177° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.37-6.87 (m, 8H), 6.06 (t, J=5.7 Hz, 1H), 4.56 (d, J=5.7 Hz, 2H), 4.46 (s, 2H), 4.05 (t, J=8.1 Hz, 2H), 3.44 (t, J=8.1 Hz, 2H), 2.58 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.5, 158.4, 157.4, 155.3, 155.2, 153.5, 135.5, 128.9, 128.3, 128.0, 127.0, 126.8, 116.8, 115.4, 48.0, 42.0, 41.6, 37.6, 17.2; MS (ES+) m/z 443.2 (M+1).

Sources & evidence

ORD record
ord-5fee0d24111b4a5ebf4be13c0edc13bb
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Linked notes

Loading…