1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(2-((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)-2-oxoethyl)-N-methylmorpholine-2-carboxamide

HRID 889217Notes

Reaction equation

HRID 889217 reaction equation
[CH3:1][NH:2][C:3]([CH:5]1[CH2:10][N:9]([CH2:11][C:12]([OH:14])=O)[CH2:8][CH2:7][O:6]1)=[O:4].[NH2:15][CH2:16][C:17]([N:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][O:29][C:30]2[C:38]3[N:37]=[C:36]([O:39][CH3:40])[N:35]([CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=4)[C:34]=3[CH:33]=[CH:32][CH:31]=2)[C:22]=1[Cl:48])[CH3:20])=[O:18].CCN=C=NCCCN(C)C>>[Cl:48][C:22]1[C:23]([CH2:28][O:29][C:30]2[C:38]3[N:37]=[C:36]([O:39][CH3:40])[N:35]([CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=4)[C:34]=3[CH:33]=[CH:32][CH:31]=2)=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[N:19]([CH3:20])[C:17](=[O:18])[CH2:16][NH:15][C:12](=[O:14])[CH2:11][N:9]1[CH2:8][CH2:7][O:6][CH:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:10]1

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 667603852-amino-N-(2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamideHCID 66760446HCID 66760446, compound

Product 1

HCID 568400184-(2-((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)-2-oxoethyl)-N-methylmorpholine-2-carboxamide

Procedure

2-(2-(methylcarbamoyl)morpholino)acetic 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 were coupled using EDCI to give 4-(2-((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)-2-oxoethyl)-N-methylmorpholine-2-carboxamide. MS (APCI) 684 (M+); 1H NMR (CDCl3) 2.26-2.40 (m, 1H), 2.61-2.82 (m, 4H), 2.95-3.15 (m, 2H), 3.15-3.28 (m, 4H), 3.40-3.49 (m, 1H), 3.61-3.91 (m, 2H), 3.90-4.01 (m, 1H), 4.08-4.18 (m, 1H), 4.22 (s, 3H), 5.28 (s, 2H), 5.62-5.70 (m, 2H), 6.51-6.58 (m, 1H), 6.75-6.87 (m, 2H), 6.91 (d, 1H, J=5.7 Hz), 7.02-7.06 (t, 1H, J=6.2 Hz), 7.19-7.21 (m, 1H), 7.31-7.33 (m, 1H), 7.46-7.49 (m, 1H), 7.55-7.62 (m, 1H), 7.78-7.90 (m, 1H), 8.57 (m, 1H). C32H35Cl2N7O6+0.8 H2O, Calculated: C, 54.97; H, 5.28; N, 14.03. Found: C, 54.99; H, 5.20; N, 13.85.

Sources & evidence

ORD record
ord-1012e8eaa1fb4662b5af7f98333f394f
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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