(1H-benzo[d]imidazol-2-yl)methanamine dihydrochloride → N-((1H-benzo[d]imidazol-2-yl)methyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamide

HRID 560883Notes

Reaction equation

HRID 560883 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.Cl.Cl.[NH:50]1[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=2[N:52]=[C:51]1[CH2:59][NH2:60]>>[NH:50]1[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=2[N:52]=[C:51]1[CH2:59][NH:60][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 2723957(1H-benzo[d]imidazol-2-yl)methanamine dihydrochlorideHCID 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 59481309N-((1H-benzo[d]imidazol-2-yl)methyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamideYield 80%

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 (1H-benzo[d]imidazol-2-yl)methanamine dihydrochloride, the title compound was obtained as a colorless solid in 80% yield: mp 265-267° C.: 1H NMR (300 MHz, DMSO-d6) δ 12.19 (br s, 1H), 8.23 (t, J=5.5 Hz, 1H), 7.54-7.46 (m, 2H), 7.38-7.31 (m, 2H), 7.24-7.10 (m, 4H), 6.25 (s, 1H), 4.60 (d, J=5.5 Hz, 2H), 4.39 (s, 2H), 3.87-3.78 (m, 2H), 3.48-3.39 (m, 2H), 2.42 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.1, 159.9, 155.5, 152.5, 142.9, 139.2, 132.9 (d, JC-F=3.0 Hz), 129.9 (d, JC-F=8.2 Hz), 121.3, 120.0, 115.3 (d, JC-F=21.2 Hz), 112.1, 46.3, 42.5, 41.3, 37.7, 15.8; MS (ES+) m/z 464.4 (M+1).

Sources & evidence

ORD record
ord-86ec0077574945afa2c8406c3ca670cc
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…