4-Fluorobenzylamine → HCID 59481260, compound

HRID 2067410Notes

Reaction equation

FC1C=CC(CN)=CC=1.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[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:16]=[CH:17][C:18]([F:19])=[C:11]([F:10])[CH:12]=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

Reactant 3

HCID 673264-Fluorobenzylamine

HCID 1235723,4-Difluorobenzylamine

HCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 59481260HCID 59481260, compoundYield 43%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 3,4-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 43% yield: mp 152-153° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.36-7.00 (m, 8H), 6.05 (s, 1H), 4.49 (d, J=5.7 Hz, 2H), 4.45 (s, 2H), 4.05 (t, J=8.4 Hz, 2H), 3.44 (t, J=8.4 Hz, 2H), 2.58 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.5, 157.3, 155.3, 153.6, 152.0, 148.6, 135.2, 128.9, 128.2, 128.1, 123.6, 117.5, 116.8, 116.7, 116.6, 47.9, 42.9, 42.0, 41.6, 17.2; MS (ES+) m/z 443.0 (M+1).

Sources & evidence

ORD record: ord-6ec5e9df27ad4e96b7ad9e36b51cc460
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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