Benzyl azide → N-benzyl-2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxamide

HRID 2381801Notes

Reaction equation

HRID 2381801 reaction equation
N(CCC1C=CC(F)=CC=1)=[N+]=[N-].[CH2:13]([N:20]=[N+:21]=[N-:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([C:38]#[CH:39])=[N:35][C:34]=1[CH3:40])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([C:38]2[N:22]=[N:21][N:20]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:39]=2)=[N:35][C:34]=1[CH3:40])=[O:32])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 12152Benzyl azideHCID 596674281-(2-Azidoethyl)-4-fluorobenzeneHCID 73213266N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide

Product 1

HCID 24962977N-benzyl-2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxamideYield 40%

Procedure

Following the procedure as described in Example 1, making variations as necessary to replace 1-(2-azidoethyl)-4-fluorobenzene with benzylazide to react with N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 40% yield: mp 108-109° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.93 (s, 1H), 7.49-7.18 (m, 10H), 6.35 (t, J=5.3 Hz, 1H), 5.51 (s, 2H), 4.56 (d, J=5.3 Hz, 2H), 2.65 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.7, 157.9, 156.6, 142.9, 137.8, 133.7, 129.3, 129.1, 128.8, 128.5, 127.8, 127.7, 124.8, 121.5, 54.6, 44.2, 17.2; MS (ES+) m/z 390.3 (M+1).

Sources & evidence

ORD record
ord-cea06b5afb664ad5842719a627abab96
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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