(2-Isopropylthiazol-4-yl)methanamine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((2-isopropylthiazol-4-yl)methyl)-4-methylthiazole-5-carboxamide

HRID 555012Notes

Reaction equation

HRID 555012 reaction equation
FC1(F)CC1CN1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O.[F:22][C:23]1[CH:44]=[CH:43][C:26]([CH2:27][N:28]2[CH2:32][CH2:31][N:30]([C:33]3[S:34][C:35]([C:39](O)=[O:40])=[C:36]([CH3:38])[N:37]=3)[C:29]2=[O:42])=[CH:25][CH:24]=1.[CH:45]([C:48]1[S:49][CH:50]=[C:51]([CH2:53][NH2:54])[N:52]=1)([CH3:47])[CH3:46]>>[F:22][C:23]1[CH:44]=[CH:43][C:26]([CH2:27][N:28]2[CH2:32][CH2:31][N:30]([C:33]3[S:34][C:35]([C:39]([NH:54][CH2:53][C:51]4[N:52]=[C:48]([CH:45]([CH3:47])[CH3:46])[S:49][CH:50]=4)=[O:40])=[C:36]([CH3:38])[N:37]=3)[C:29]2=[O:42])=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 16427107(2-Isopropylthiazol-4-yl)methanamineHCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 579198122-(3-((2,2-Difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579199532-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((2-isopropylthiazol-4-yl)methyl)-4-methylthiazole-5-carboxamideYield 68%

Procedure

Following the procedure as describe in Example 16, making variations as required to replace 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with (2-isopropylthiazol-4-yl)methanamine, the title compound was obtained as a colourless solid in 68% yield: mp 170-172° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.45 (t, J=5.8 Hz, 1H), 7.35-7.30 (m, 2H), 7.19-7.14 (m, 3H), 4.41-4.39 (m, 4H), 3.97 (t, J=9.0 Hz, 2H), 3.42 (t, J=9.0 Hz, 2H), 3.26-3.15 (m, 1H), 2.44 (s, 3H), 1.28 (d, J=6.0 Hz, 6H); 13C NMR (75 MHz, DMSO-d6) δ 177.2, 163.6, 162.2, 160.4, 157.9, 155.5, 154.0, 133.0 (d), 130.4 (d), 118.4, 115.9, 113.8, 46.6, 42.4, 42.0, 32.9, 23.3, 17.5; MS (ES+) m/z 474.0 (M+1).

Sources & evidence

ORD record
ord-074e8e620fd24fc29341bc20df29c560
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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