1-(Azidomethyl)-4-fluorobenzene → N-benzyl-2-(1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxamide

HRID 2381802Notes

Reaction equation

HRID 2381802 reaction equation
N(CCC1C=CC(F)=CC=1)=[N+]=[N-].[N:13]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[N+:14]=[N-:15].[CH2:24]([NH:31][C:32]([C:34]1[S:38][C:37]([C:39]#[CH:40])=[N:36][C:35]=1[CH3:41])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([NH:31][C:32]([C:34]1[S:38][C:37]([C:39]2[N:15]=[N:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:40]=2)=[N:36][C:35]=1[CH3:41])=[O:33])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 112058641-(Azidomethyl)-4-fluorobenzeneHCID 596674281-(2-Azidoethyl)-4-fluorobenzeneHCID 73213266N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide

Product 1

HCID 24962978N-benzyl-2-(1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxamideYield 59%

Procedure

Following the procedure as described in Example 1, making variations as necessary to replace 1-(2-azidoethyl)-4-fluorobenzene with 1-(azidomethyl)-4-fluorobenzene to react with N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 59% yield: mp 114-115° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.96 (s, 1H), 7.45-7.19 (m, 7H), 7.12-6.99 (m, 2H), 6.19 (t, J=5.6 Hz, 1H), 5.51 (s, 2H), 4.58 (d, J=5.6 Hz, 2H), 2.66 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.9, 161.7, 157.8, 155.5, 142.9, 137.9, 130.3, 129.6, 128.7, 127.8, 127.6, 125.0, 121.9, 115.3, 53.8, 44.1, 17.2; MS (ES+) m/z 408.3 (M+1).

Sources & evidence

ORD record
ord-4578555999a3473ea501632aedbc4fdf
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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