3-(6-(Methylcarbamoyl)pyridin-3-yl)propanoic acid → 5-(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-methyl-1,4,5,6-tetrahydropyrimidine-2-carboxamide

HRID 889208Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1C=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:7][N:6]=1)=[O:4].[NH2:16][CH2:17][C:18]([N:20]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([CH2:29][O:30][C:31]2[C:39]3[N:38]=[C:37]([O:40][CH3:41])[N:36]([CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=4)[C:35]=3[CH:34]=[CH:33][CH:32]=2)[C:23]=1[Cl:49])[CH3:21])=[O:19].ClC1C(COC2C3N=C(OC)[N:64](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:49][C:23]1[C:24]([CH2:29][O:30][C:31]2[C:39]3[N:38]=[C:37]([O:40][CH3:41])[N:36]([CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=4)[C:35]=3[CH:34]=[CH:33][CH:32]=2)=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[N:20]([CH3:21])[C:18](=[O:19])[CH2:17][NH:16][C:13](=[O:15])[CH2:12][CH2:11][CH:8]1[CH2:7][NH:6][C:5]([C:3]([NH:2][CH3:1])=[O:4])=[N:64][CH2:9]1

Participants

Reactant 3

HCID 667602213-(6-(Methylcarbamoyl)pyridin-3-yl)propanoic acid

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 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 667612225-(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-methyl-1,4,5,6-tetrahydropyrimidine-2-carboxamide

Procedure

3-(2-methylcarbamoyl-pyridine-5-yl)-propionic 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 as described for compound 1. MS (APCI) 695 (M+), 1HNMR (400 MHz, MeOD) δ 1.57-1.69 (m, 3H), 2.31 (m, 2H), 2.78 (s, 3H), 2.98 (m, 2H), 3.19 (s, 3H), 3.34-3.824 (m, 4H), 4.30 (s, 3H), 5.30 (s, 2H), 5.55 (m, 2H), 6.83 (m, 2H), 7.05 (m, 2H), 7.30 (m, 1H), 7.57 (m, 2H), 7.63 (m, 1H), 8.49 (d, 1H). C33H36Cl2N8O5+0.4 H2O, Calculated: C, 56.4; H, 5.28; N, 15.94. Found: C, 56.4; H, 5.35; N, 15.90.

Sources & evidence

ORD record: ord-1b4a2aa08f764569be0c14f66dc279ab
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252793B2

Reaction notes

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