(2-Isopropylthiazol-4-yl)methanamine → N-((2-isopropylthiazol-4-yl)methyl)-4-methyl-2-(1-(4-methylbenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxamide

HRID 555015Notes

Reaction equation

HRID 555015 reaction equation
F[C:2]1(F)CC1CN1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O.F[C:23]1[CH:44]=[CH:43][C:26]([CH2:27][N:28]2[C:32](=[O:33])[N:31]([C:34]3[S:35][C:36]([C:40]([OH:42])=O)=[C:37]([CH3:39])[N:38]=3)[CH:30]=[N:29]2)=[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]>>[CH:45]([C:48]1[S:49][CH:50]=[C:51]([CH2:53][NH:54][C:40]([C:36]2[S:35][C:34]([N:31]3[C:32](=[O:33])[N:28]([CH2:27][C:26]4[CH:25]=[CH:24][C:23]([CH3:2])=[CH:44][CH:43]=4)[N:29]=[CH:30]3)=[N:38][C:37]=2[CH3:39])=[O:42])[N:52]=1)([CH3:47])[CH3:46]

Participants

4

Reactant 3

HCID 16427107(2-Isopropylthiazol-4-yl)methanamineHCID 579198022-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidHCID 579198122-(3-((2,2-Difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 66661357N-((2-isopropylthiazol-4-yl)methyl)-4-methyl-2-(1-(4-methylbenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxamideYield 61%

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-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid to react with (2-isopropylthiazol-4-yl)methanamine, the title compound was obtained as a colourless solid in 61% yield: mp 151-153° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.81 (t, J=5.8 Hz, 1H), 8.73 (s, 1H), 7.33-7.30 (m, 2H), 7.20 (s, 1H), 7.19-7.13 (m, 2H), 4.97 (s, 2H), 4.44 (d, J=6.0 Hz, 2H), 3.63-3.53 (m, 1H), 2.54 (s, 3H), 1.28 (d, J=6.0 Hz, 6H); 13C NMR (75 MHz, DMSO-d6) δ 177.3, 162.2 (d), 161.3, 153.6, 151.8, 151.4, 150.2, 132.7 (d), 132.5, 130.4 (d), 123.0, 115.9, 114.1, 48.2, 42.3, 32.9, 23.3, 17.4; MS (ES+) m/z 472.9 (M+1).

Sources & evidence

ORD record
ord-de8b44dd778b4637bf0ae1aa27bab46a
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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