4-Fluorobenzyl bromide → Ethyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylate

HRID 560787Notes

Reaction equation

HRID 560787 reaction equation
O=C1NCCN1C1SC(C([O-])=O)=CN=1.[O:15]=[C:16]1[NH:20][CH2:19][CH2:18][N:17]1[C:21]1[S:22][C:23]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=1.Br[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1>>[F:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][N:20]2[CH2:19][CH2:18][N:17]([C:21]3[S:22][C:23]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=3)[C:16]2=[O:15])=[CH:38][CH:39]=1

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 59481234Ethyl 2-(2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylateHCID 86645291HCID 86645291, compound

Product 1

HCID 59481310Ethyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylateYield 94%

Procedure

Following the procedure as described in Example 24, making variations as required to replace 2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate with ethyl 2-(2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylate to react with 1-(bromomethyl)-4-fluorobenzene, the title compound was obtained as a colorless solid in 94% yield: 1H NMR (300 MHz, CDCl3) δ 7.28-7.25 (m, 2H), 7.06-7.01 (m, 2H), 4.46 (s, 2H), 4.33 (q, J=7.1 Hz, 2H), 4.13-4.07 (m, 2H), 3.50-3.44 (m, 2H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 418.1 (M+1).

Sources & evidence

ORD record
ord-f60a9434b20c4c4e84cb3f233cde4576
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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