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

HRID 2381819Notes

Reaction equation

HRID 2381819 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][CH:5]=CC=1.C1(CC[N:27]2[CH:31]=[C:30]([C:32]3S[C:34]([C:38](O)=O)=[C:35](C)[N:36]=3)N=N2)CC1.N1C=CC=C(CN)C=1>>[CH:7]1([CH2:2][CH2:1][N:8]2[CH:12]=[C:11]([C:13]3[S:14][C:15]([C:19]([NH:27][CH2:31][C:30]4[CH:32]=[N:36][CH:35]=[CH:34][CH:38]=4)=[O:21])=[C:16]([CH3:18])[N:17]=3)[N:10]=[N:9]2)[CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 591796642-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acidHCID 591796752-(1-(2-cyclopropylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 249574762-(1-(2-cyclopropylethyl)-1H-1,2,3-triazol-4-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 19%

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-(2-cyclopropylethyl)-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 19% yield: mp 124-125° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.52 (s, 1H), 8.09 (s, 1H), 7.33-7.22 (m, 2H), 6.33 (t, J=5.7 Hz, 1H), 4.62 (d, J=5.7 Hz, 2H), 4.48 (t, J=7.0 Hz, 2H), 2.71 (s, 3H), 1.82 (q, J=7.0 Hz, 2H), 0.71-0.56 (m, 1H), 0.52-0.43 (m, 2H), 0.08-0.01 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 161.9, 158.3, 157.3, 149.3, 149.1, 142.4, 135.7, 133.6, 124.1, 123.7, 121.8, 51.1, 41.6, 35.1, 17.4, 8.1, 4.3; MS (ES+) m/z 369.3 (M+1).

Sources & evidence

ORD record
ord-3789ecb792e34161adf30c6f8e272fc9
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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