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-methylpyrimidine-2-carboxamide

HRID 889210Notes

Reaction equation

HRID 889210 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][C:8]1[CH:9]=[N:64][C:5]([C:3]([NH:2][CH3:1])=[O:4])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 667602213-(6-(Methylcarbamoyl)pyridin-3-yl)propanoic acidHCID 667603852-amino-N-(2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamideHCID 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 680264295-(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-methylpyrimidine-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 and coupled together as described for compound 1 above. LCMS (APCI) 691 (M+1); 1HNMR (400 MHz, MeOD) δ 2.90-3.0 (m, 5H), 3.21-3.25 (m, 5H), 3.66 (d, 1H), 3.96 (d, 1H), 4.15 (s, 3H), 5.33 (s, 2H), 5.58 (m, 2H), 6.86 (m, 2H), 7.08 (m, 2H), 7.32 (m, 1H), 7.55-762(m, 2H), 7.76 (m, 1H), 8.51 (d, 1H), 9.08 (s, 2H)

Sources & evidence

ORD record
ord-ce8e329b5ad84b13ab9e37613ef6863c
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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