2-amino-N-(2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamide → N-(2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)-3-(6-(methylsulfonamido)pyridin-3-yl)propanamide

HRID 889175Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[NH2:17][CH2:18][C:19]([N:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([CH2:30][O:31][C:32]2[C:40]3[N:39]=[C:38]([O:41][CH3:42])[N:37]([CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=4)[C:36]=3[CH:35]=[CH:34][CH:33]=2)[C:24]=1[Cl:50])[CH3:22])=[O:20].ClC1C(COC2C3N=C(OC)N(CC4C=CC=CN=4)C=3C=CC=2)=C(Cl)C=CC=1N(C)C(=O)CNC(=O)CCC1C=CC(C(NCCOC)=O)=CC=1>>[Cl:50][C:24]1[C:25]([CH2:30][O:31][C:32]2[C:40]3[N:39]=[C:38]([O:41][CH3:42])[N:37]([CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=4)[C:36]=3[CH:35]=[CH:34][CH:33]=2)=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[N:21]([CH3:22])[C:19](=[O:20])[CH2:18][NH:17][C:14](=[O:16])[CH2:13][CH2:12][C:9]1[CH:10]=[N:11][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 667603852-amino-N-(2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamide

HCID 667605946-[(Methylsulfonyl)amino]-3-pyridinepropanoic acid

HCID 667609784-(3-((2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-(2-methoxyethyl)benzamide

Product 1

HCID 66761221N-(2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)-3-(6-(methylsulfonamido)pyridin-3-yl)propanamide

Procedure

Compound 5 was prepared from 3-(6-(methylsulfonamido)pyridin-3-yl)propanoic acid and 2-amino-N-(2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamide described for compound 1. MS (APCI) 737(M+), 1H NMR (CDCl3) 2.41-2.51 (m, 2H), 2.65 (s, 3H), 2.81-2.92 (m, 2H), 3.05 (s, 3H), 3.22 (s, 3H), 3.33-3.52 (m, 1H), 3.37-3.90 (m, 1H), 5.40 (s, 2H), 5.61 (s, 2H), 6.50-6.61 (m, 1H), 6.71 (s, 1H), 7.17-7.3 (m, 4H), 7.34-7.42 (m, 1H), 7.42-7.52 (m, 1H), 7.55-7.63 (m, 2H), 7.70-7.80 (m, 1H), 7.82-7.95 (m, 1H), 8.04 (s, 1H), 8.61-8.68 (m, 1H).

Sources & evidence

ORD record: ord-765fdfd061af4e1e8141af511b93b9c9
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252793B2

Reaction notes

Loading…