1-(Azidomethyl)-4-(trifluoromethyl)benzene → N-benzyl-4-methyl-2-(1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)thiazole-5-carboxamide

HRID 2381803Notes

Reaction equation

HRID 2381803 reaction equation
N(CCC1C=CC(F)=CC=1)=[N+]=[N-].[N:13]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)=[N+:14]=[N-:15].[CH2:27]([NH:34][C:35]([C:37]1[S:41][C:40]([C:42]#[CH:43])=[N:39][C:38]=1[CH3:44])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([NH:34][C:35]([C:37]1[S:41][C:40]([C:42]2[N:15]=[N:14][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:21][CH:22]=3)[CH:43]=2)=[N:39][C:38]=1[CH3:44])=[O:36])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 498459471-(Azidomethyl)-4-(trifluoromethyl)benzeneHCID 596674281-(2-Azidoethyl)-4-fluorobenzeneHCID 73213266N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide

Product 1

HCID 24962979N-benzyl-4-methyl-2-(1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)thiazole-5-carboxamideYield 81%

Procedure

Following the procedure as described in Example 1, making variations as necessary to replace 1-(2-azidoethyl)-4-fluorobenzene with 1-(azidomethyl)-4-(trifluoromethyl)benzene to react with N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 81% yield: mp 131-132° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.98 (s, 1H), 7.65-7.53 (m, 2H), 7.45-7.34 (m, 2H), 7.28-7.19 (m, 5H), 6.60 (t, J=5.6 Hz, 1H), 5.57 (s, 2H), 4.54 (d, J=5.6 Hz, 2H), 2.61 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.9, 157.6, 155.5, 143.1, 137.9, 137.8, 131.3, 128.8, 128.6, 127.8, 127.6, 126.5, 125.2, 123.7, 121.7, 53.8, 44.1, 17.2; MS (ES+) m/z 458.3 (M+1).

Sources & evidence

ORD record
ord-4431c309e3744c28a04cd919cd940137
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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