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

HRID 560763Notes

Reaction equation

HRID 560763 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[C:14](=[O:15])[N:13]([CH2:16][C:17]3[CH:22]=[CH:21]C(C(F)(F)F)=CC=3)[N:12]=[CH:11]2)[S:5][C:6]=1[C:7]([OH:9])=O.C1(CN2C(=O)N(C3SC(C(O)=O)=C(C)N=3)C=N2)CC1.[N:46]1[CH:51]=[CH:50][CH:49]=[C:48]([CH2:52][NH2:53])[CH:47]=1>>[CH:17]1([CH2:16][N:13]2[C:14](=[O:15])[N:10]([C:4]3[S:5][C:6]([C:7]([NH:53][CH2:52][C:48]4[CH:47]=[N:46][CH:51]=[CH:50][CH:49]=4)=[O:9])=[C:2]([CH3:1])[N:3]=3)[CH:11]=[N:12]2)[CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579197562-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidHCID 580316664-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylic acid

Product 1

HCID 250956752-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 49%

Procedure

Following the procedure as described in Example 21, making variations as required to replace 4-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylic acid with 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 49% yield: mp 116-117° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.57 (br s, 1H), 8.47 (br s, 1H), 8.24 (s, 1H), 7.79-7.71 (m, 1H), 7.44-7.27 (m, 1H), 6.38 (t, J=5.8 Hz, 1H), 4.62 (d, J=5.8 Hz, 2H), 3.70 (d, J=7.2 Hz, 2H), 2.65 (s, 3H), 1.34-1.14 (m, 1H), 0.63-0.52 (m, 2H), 0.46-0.31 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 161.8, 153.4, 151.2, 149.9, 149.2, 148.9, 135.8, 130.5, 123.8, 121.4, 117.9, 50.6, 41.6, 17.2, 10.2, 3.7; MS (ES+) m/z 371.3 (M+1).

Sources & evidence

ORD record
ord-38c7b9d44256482395857c879d4c6687
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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