4-Fluorobenzylamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide

HRID 560646Notes

Reaction equation

HRID 560646 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6]C=CC=1.C1(CN2CCN(C3SC(C(O)=O)=C(C)N=3)C2=O)CC1.[F:42][C:43]1[CH:50]=[CH:49][C:46]([CH2:47][NH2:48])=[CH:45][CH:44]=1>>[CH:2]1([CH2:1][N:8]2[CH2:12][CH2:11][N:10]([C:13]3[S:14][C:15]([C:19]([NH:48][CH2:47][C:46]4[CH:49]=[CH:50][C:43]([F:42])=[CH:44][CH:45]=4)=[O:21])=[C:16]([CH3:18])[N:17]=3)[C:9]2=[O:22])[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 250948762-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamideYield 76%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with 4-fluorobenzylamine in place of benzylamine, the title compound was obtained as a white powder in 76% yield: mp 146-147° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.27-7.23 (m, 2H), 7.00-6.94 (m, 2H), 6.01 (t, J=5.4 Hz, 1H), 4.48 (d, J=5.4 Hz, 2H), 4.06 (t, J=8.4 Hz, 2H), 3.67 (t, J=8.4 Hz, 2H), 3.13 (d, J=7.2 Hz, 2H), 2.57 (s, 3H), 0.95-0.84 (m, 1H), 0.56-0.48 (m, 2H), 0.23-0.18 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 162.5, 162.1, 157.4, 155.2, 153.2, 133.9, 129.5, 116.8, 115.6, 48.6, 43.2, 42.2, 42.1, 17.2, 8.9, 3.4; MS (ES+) m/z 389.2 (M+1).

Sources & evidence

ORD record
ord-f71a145f87f546d7982dc2012827bdda
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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