2-amino-N-(2,4-dimethyl-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamide → methyl (5-(3-((2-((3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)-2,4-dimethylphenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)pyridin-2-yl)carbamate

HRID 889174Notes

Reaction equation

HRID 889174 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([CH2:14][O:15][C:16]2[C:24]3[N:23]=[C:22]([O:25][CH3:26])[N:21]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[C:20]=3[CH:19]=[CH:18][CH:17]=2)[C:8]=1[CH3:34])[CH3:6])=[O:4].[CH3:35][O:36][C:37]([NH:39][C:40]1[N:45]=[CH:44][C:43]([CH2:46][CH2:47][C:48](O)=[O:49])=[CH:42][CH:41]=1)=[O:38]>>[CH3:26][O:25][C:22]1[N:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:15][CH2:14][C:9]3[C:8]([CH3:34])=[C:7]([N:5]([CH3:6])[C:3](=[O:4])[CH2:2][NH:1][C:48](=[O:49])[CH2:47][CH2:46][C:43]4[CH:42]=[CH:41][C:40]([NH:39][C:37](=[O:38])[O:36][CH3:35])=[N:45][CH:44]=4)[CH:12]=[CH:11][C:10]=3[CH3:13])[C:24]=2[N:23]=1

Participants

3

Reactant 2

HCID 667599582-amino-N-(2,4-dimethyl-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamideHCID 667607703-(6-((Methoxycarbonyl)amino)pyridin-3-yl)propanoic acid

Product 1

HCID 68026363methyl (5-(3-((2-((3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)-2,4-dimethylphenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)pyridin-2-yl)carbamate

Procedure

2-amino-N-(3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)-2,4-dimethylphenyl)-N-methylacetamide and 3-(6-((methoxycarbonyl)amino)pyridin-3-yl)propanoic acid were used to prepare 4 using the method described for 1. LCMS (+APCI) 666 (M+). 1H-NMR (CDCl3, δ ppm): 1H-NMR (CDCl3, δ ppm): 8.58 (m, 1H), 8.06 (d, J=1.6 Hz, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.55 (m, 3H), 7.20 (m, 1H), 7.13 (d, J=8.0 Hz, 1H), 7.03 (m, 2H), 6.93 (d, J=8.0 Hz, 1H), 6.81 (m, 2H), 6.43 (bt, J=4.0 Hz, 1H), 5.41 (s, 2H), 5.28 (s, 2H), 4.20 (s, 3H), 3.79 (s, 3H), 3.69 (dd, J=4.4, 18.0 Hz, 1H), 3.47 (dd, J=4.0, 18.0 Hz, 1H), 3.21 (s, 3H), 2.88 (t, J=7.6 Hz, 2H), 2.49 (s, 3H), 2.47 (m, 2H), 2.31 (s, 3H). Calcd. for C36H39N7O6+0.8H2O: C, 63.57; H, 6.02; N, 14.42. Found: C, 63.64; H, 5.93; N, 14.53.

Workup

  1. customto prepare 4 using the method

Sources & evidence

ORD record
ord-7b9c6f599eb2468595379403f4fd1bd2
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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