1,3-Thiazol-2-ylmethanamine → 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(thiazol-2-ylmethyl)thiophene-2-carboxamide

HRID 560899Notes

Reaction equation

HRID 560899 reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(O)=O.[F:25][C:26]1[CH:47]=[CH:46][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:40][C:39]([C:41]([OH:43])=O)=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.[S:48]1[CH:52]=[CH:51][N:50]=[C:49]1[CH2:53][NH2:54]>>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:40][C:39]([C:41]([NH:54][CH2:53][C:49]4[S:48][CH:52]=[CH:51][N:50]=4)=[O:43])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:46][CH:47]=1

Participants

4

Reactant 3

HCID 27565071,3-Thiazol-2-ylmethanamineHCID 580314563-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acidHCID 580314655-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 250971895-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(thiazol-2-ylmethyl)thiophene-2-carboxamideYield 48%

Procedure

Following the procedures as described in Example 55, making variations as required to replace 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with thiazol-2-ylmethanamine, the title compound was obtained as a colorless solid in 48% yield: 1H NMR (300 MHz, CDCl3) δ 7.72 (d, J=3.3 Hz, 1H), 7.31-7.23 (m, 3H), 7.07-6.99 (m, 2H), 6.50 (t, J=5.4 Hz, 1H), 6.12 (s, 1 H), 4.90 (d, J=5.4 Hz, 2H), 4.43 (s, 2H), 3.84-3.75 (m, 2H), 3.47-3.39 (m, 2H), 2.50 (s, 3H); MS (ES+) m/z 453.1 (M+23).

Sources & evidence

ORD record
ord-e0bdae5e27cf41b3ac5980f3538e2195
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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