1,3-benzothiazol-2-ylmethylamine → N-(benzo[d]thiazol-2-ylmethyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamide

HRID 560889Notes

Reaction equation

HRID 560889 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[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=2[N:50]=[C:49]1[CH2:57][NH2:58]>>[S:48]1[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=2[N:50]=[C:49]1[CH2:57][NH:58][C:41]([C:39]1[S:40][C:36]([N:33]2[CH2:34][CH2:35][N:31]([CH2:30][C:29]3[CH:28]=[CH:27][C:26]([F:25])=[CH:47][CH:46]=3)[C:32]2=[O:45])=[CH:37][C:38]=1[CH3:44])=[O:43]

Participants

4

Reactant 3

HCID 3504141,3-benzothiazol-2-ylmethylamineHCID 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 59481214N-(benzo[d]thiazol-2-ylmethyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamideYield 81%

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 benzo[d]thiazol-2-ylmethanamine, the title compound was obtained as a colorless solid in 81% yield: 1H NMR (300 MHz, CDCl3) δ 8.00 (d, J=8.0 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.51-7.44 (m, 1H), 7.41-7.34 (m, 1H), 7.31-7.24 (m, 2H), 7.07-6.98 (m, 2H), 6.63 (t, J=5.5 Hz, 1H), 6.13 (s, 1H), 5.01 (d, J=5.5 Hz, 2H), 4.44 (s, 2H), 3.84-3.76 (m, 2H), 3.48-3.40 (m, 2H), 2.53 (s, 3H); MS (ES+) m/z 481.2 (M+1).

Sources & evidence

ORD record
ord-db07457ff73b46c6bba4bd2ba4784021
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…