N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamide → 2-(3-(4-fluorophenethyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560732Notes

Reaction equation

HRID 560732 reaction equation
C(NC(C1SC(NC(N(CC(OC)OC)CC2C=CC(F)=CC=2)=O)=NC=1C)=O)C1C=CC=CC=1.CO[CH:37]([O:68]C)[CH2:38][N:39]([CH2:59][CH2:60][C:61]1[CH:66]=[CH:65][C:64]([F:67])=[CH:63][CH:62]=1)[C:40](=[O:58])[NH:41][C:42]1[S:43][C:44]([C:48]([NH:50][CH2:51][C:52]2[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=2)=[O:49])=[C:45]([CH3:47])[N:46]=1>>[F:67][C:64]1[CH:63]=[CH:62][C:61]([CH2:60][CH2:59][N:39]2[CH2:38][CH:37]([OH:68])[N:41]([C:42]3[S:43][C:44]([C:48]([NH:50][CH2:51][C:52]4[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=4)=[O:49])=[C:45]([CH3:47])[N:46]=3)[C:40]2=[O:58])=[CH:66][CH:65]=1

Participants

3

Reactant 2

HCID 86645286N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamideHCID 866452872-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Product 1

HCID 250961892-(3-(4-fluorophenethyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 21%

Procedure

Following the procedure as described in Example 16, making variations as required to replace N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamide with 2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide the title compound was obtained as a colorless solid in 21% yield: mp 182-184° C. (ethyl acetate): 1H NMR (300 MHz, CDCl3) δ 8.61-8.48 (m, 2H), 7.67 (d, J=7.2 Hz, 1H), 7.28 (br s, 1H), 7.18-7.03 (m, 2H), 6.97 (d, J=8.6 Hz, 2H), 6.12-5.93 (m, 2H), 4.72 (br s, 1H), 4.57 (d, J=5.7 Hz, 2H) 3.65-3.45 (m, 3H), 3.34-3.29 (m, 1H), 2.85 (t, J=7.2 Hz, 2H), 2.57 (s, 3H): 13C NMR (75 MHz, CDCl3) δ 162.3, 160.1, 157.1, 153.4, 153.3, 149.2, 149.0, 135.6, 133.6, 130.1, 130.0, 117.2, 115.7, 115.4, 77.2, 50.2, 44.8, 41.4, 33.1, 17.2; MS (ES+) m/z 456.3 (M+1).

Sources & evidence

ORD record
ord-6a5799c0e48d40f9a9e9a015fd2eff50
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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