(R)-ethyl 2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate → HCID 57919858, compound

HRID 554889Notes

Reaction equation

HRID 554889 reaction equation
FC1C=CC(CN2[C@@H](C)CN(C3SC(C(OCC)=O)=C(C)N=3)C2=O)=CC=1.[F:27][C:28]1[CH:52]=[CH:51][C:31]([CH2:32][N:33]2[CH2:37][C@@H:36]([CH3:38])[N:35]([C:39]3[S:40][C:41]([C:45]([O:47]CC)=[O:46])=[C:42]([CH3:44])[N:43]=3)[C:34]2=[O:50])=[CH:30][CH:29]=1>>[F:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:32][N:33]2[CH2:37][C@@H:36]([CH3:38])[N:35]([C:39]3[S:40][C:41]([C:45]([OH:47])=[O:46])=[C:42]([CH3:44])[N:43]=3)[C:34]2=[O:50])=[CH:51][CH:52]=1

Participants

3

Reactant 2

HCID 57919748(R)-ethyl 2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateHCID 57919865(S)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 57919858HCID 57919858, compound

Procedure

Following the procedure as described in Preparation 6, making variations as required to replace (S)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate with (R)-ethyl 2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a colorless solid (73%): mp 184-186° C.; 1H NMR (300 MHz, DMSO-d6) δ 12.83 (s, 1H), 7.37-7.32 (m, 2H), 7.22-7.16 (m, 2H), 4.58-4.51 (m 1H), 4.46 (d, J=15.2 Hz, 1H), 4.38 (d, J=15.2 Hz, 1H), 3.61 (t, J=9.0 Hz, 1H), 3.03 (dd, J=9.0, 3.3 Hz, 1H), 2.50 (s, 3H), 1.38 (d, J=6.2 Hz, 3H); (ES+) m/z 349.7 (M+1).

Workup

  1. customas described in Preparation 6

Sources & evidence

ORD record
ord-0054f5e4fa804d5eaa975af13f9cb460
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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