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

HRID 2381818Notes

Reaction equation

HRID 2381818 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2S[C:15]([C:19](O)=O)=[C:16](C)[N:17]=2)N=N1)C1C=CC=CC=1.[F:22][C:23]1[CH:44]=[CH:43][C:26]([CH2:27][CH2:28][N:29]2[CH:33]=[C:32]([C:34]3[S:35][C:36]([C:40]([OH:42])=O)=[C:37]([CH3:39])[N:38]=3)[N:31]=[N:30]2)=[CH:25][CH:24]=1.N1C=CC=C(CN)C=1>>[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][CH2:28][N:29]2[CH:33]=[C:32]([C:34]3[S:35][C:36]([C:40]([NH:8][CH2:12][C:11]4[CH:13]=[N:17][CH:16]=[CH:15][CH:19]=4)=[O:42])=[C:37]([CH3:39])[N:38]=3)[N:31]=[N:30]2)=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 591796642-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acidHCID 591796862-(1-(4-fluorophenethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 249574752-(1-(4-fluorophenethyl)-1H-1,2,3-triazol-4-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 53%

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-(4-fluorophenethyl)-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 53% yield: mp 149-150° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.50 (br s, 1H), 8.42 (br s, 1H), 7.84 (s, 1H), 7.70-7.62 (m, 1H), 7.27-7.16 (m, 1H), 7.12-6.99 (m, 3H), 6.95-6.85 (m, 2H), 4.56 (t, J=7.1 Hz, 2H), 4.55 (d, J=5.5 Hz, 2H), 3.16 (t, J=7.1 Hz, 2H), 2.63 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.0, 161.9, 157.9, 157.1, 149.2, 148.8, 142.4, 135.7, 133.9, 132.2, 132.1, 130.1, 124.1, 121.9, 115.8, 52.0, 41.5, 35.7, 17.3; MS (ES+) m/z 423.3 (M+1).

Sources & evidence

ORD record
ord-439d6192ea6f49ceaefb95afb5adc517
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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