(1,5-dimethyl-1H-pyrrol-2-yl)methanamine → N-((1,5-dimethyl-1H-pyrrol-2-yl)methyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamide

HRID 2067680Notes

Reaction equation

HRID 2067680 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](O)=[O:42])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.[CH3:48][N:49]1[C:53]([CH3:54])=[CH:52][CH:51]=[C:50]1[CH2:55][NH2:56]>>[CH3:48][N:49]1[C:53]([CH3:54])=[CH:52][CH:51]=[C:50]1[CH2:55][NH:56][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:42]

Participants

4

Reactant 3

HCID 737232(1,5-dimethyl-1H-pyrrol-2-yl)methanamineHCID 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 25097190N-((1,5-dimethyl-1H-pyrrol-2-yl)methyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamideYield 57%

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 (1,5-dimethyl-1H-pyrrol-2-yl)methanamine, the title compound was obtained as a beige solid in 57% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.07-6.98 (m, 2H), 6.08 (s, 1H), 6.00 (d, J=3.2 Hz, 1H), 5.81 (d, J=3.2 Hz, 1H), 5.67 (t, J=4.4 Hz, 1H), 4.53 (d, J=4.4 Hz, 2H), 4.42 (s, 2H), 3.83-3.74 (m, 2H), 3.49-3.39 (m, 5H), 2.48 (s, 3H), 2.21 (s, 3H); MS (ES+) m/z 463.1 (M+23).

Sources & evidence

ORD record
ord-755e5f99042845459e7ac39cba3f09f8
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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