N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide → 2-(3-(4-fluorophenethyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560736Notes

Reaction equation

HRID 560736 reaction equation
C(NC(C1SC(N2C(O)CN(CC3C=CC(F)=CC=3)C2=O)=NC=1C)=O)C1C=CC=CC=1.[F:32][C:33]1[CH:63]=[CH:62][C:36]([CH2:37][CH2:38][N:39]2[CH2:43][CH:42](O)[N:41]([C:45]3[S:46][C:47]([C:51]([NH:53][CH2:54][C:55]4[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=4)=[O:52])=[C:48]([CH3:50])[N:49]=3)[C:40]2=[O:61])=[CH:35][CH:34]=1>>[F:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:37][CH2:38][N:39]2[CH:43]=[CH:42][N:41]([C:45]3[S:46][C:47]([C:51]([NH:53][CH2:54][C:55]4[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=4)=[O:52])=[C:48]([CH3:50])[N:49]=3)[C:40]2=[O:61])=[CH:62][CH:63]=1

Participants

3

Reactant 2

HCID 25095416N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamideHCID 250961892-(3-(4-fluorophenethyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Product 1

HCID 594813022-(3-(4-fluorophenethyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 14%

Procedure

Following the procedure as described in Example 17, making variations as required to replace N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide with 2-(3-(4-fluorophenethyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide 2, the title compound was obtained as a colorless solid in 14% yield: mp 160-162° C. (ethyl acetate/hexanes): 1H NMR (300 MHz, DMSO-d6) δ 8.72 (d, J=5.8 Hz, 1H), 8.50-8.49 (m, 1H), 8.42 (dd, J=4.7, 1.8 Hz, 1H), 7.68 (td, J=7.8, 1.8 Hz, 1H), 7.34-7.30 (m, 1H), 7.22-7.17 (m, 3H), 7.11-7.03 (m, 2H), 6.84 (d, J=3.2 Hz, 1H), 4.38 (d, J=5.8 Hz, 2H), 3.83 (t, J=7.1 Hz, 2H), 2.92 (t, J=7.1 Hz, 2H), 2.48 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.0, 161.9, 159.8, 153.8, 151.6, 150.3, 149.3, 148.5, 135.6, 135.3, 134.6, 131.0, 123.9, 120.7, 115.7, 106.7, 44.6, 40.9, 33.8, 17.4; MS (ES+) m/z 438.3 (M+1).

Sources & evidence

ORD record
ord-ce887cbf9f27446fb01377e846e61b88
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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