3-Pyridinemethanamine → 2-(1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 2381820Notes

Reaction equation

HRID 2381820 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:14][C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6]C=CC=1.C1(C[N:26]2[CH:30]=[C:29]([C:31]3S[C:33]([C:37](O)=O)=[C:34](C)[N:35]=3)N=N2)CC1.N1C=CC=C(CN)C=1>>[CH:2]1([CH2:1][N:8]2[CH:12]=[C:11]([C:13]3[S:14][C:15]([C:19]([NH:26][CH2:30][C:29]4[CH:31]=[N:35][CH:34]=[CH:33][CH:37]=4)=[O:21])=[C:16]([CH3:18])[N:17]=3)[N:10]=[N:9]2)[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 591796642-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acidHCID 591797252-(1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 249574772-(1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 57%

Procedure

Following the procedure as described in Example 4, making variations as necessary to replace 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid with 2-(1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 57% yield: mp 140-141° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.73-8.48 (m, 2H), 8.24 (s, 1H), 7.76-7.66 (m, 1H), 7.39-7.19 (m, 1H), 6.71 (br s, 1H), 4.62 (d, J=5.3 Hz, 2H), 4.26 (d, J=7.2 Hz, 2H), 2.72 (s, 3H), 1.39-1.23 (m, 1H), 0.81-0.66 (m, 2H), 0.53-0.38 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 161.9, 158.3, 157.3, 149.2, 148.9, 143.9, 142.5, 135.8, 133.8, 124.1, 121.2, 55.5, 41.6, 17.3, 10.8, 4.4; MS (ES+) m/z 355.3 (M+1).

Sources & evidence

ORD record
ord-c8afd3d3e53b4ffda9d58c24c103a493
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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