3-(4-(Methylcarbamoyl)piperazin-1-yl)propanoic acid → 4-(3-((2-((2,4-dichloro-3-(((2-ethyl-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylpiperazine-1-carboxamide

HRID 889189Notes

Reaction equation

HRID 889189 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([CH:14]([O:22][C:23]2[C:31]3[N:30]=[C:29]([CH2:32][CH3:33])[NH:28][C:27]=3[CH:26]=[CH:25][CH:24]=2)CC2C=CC=CN=2)[C:8]=1[Cl:34])[CH3:6])=[O:4].[CH3:35][NH:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][C:47]([OH:49])=O)[CH2:41][CH2:40]1)=[O:38].ClC1C(COC2C3N=C(OC)N([CH2:70][C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=4)C=3C=CC=2)=C(Cl)C=CC=1N(C)C(=O)CNC(=O)CCC1C=CC(C(NCCOC)=O)=CC=1>>[Cl:34][C:8]1[C:9]([CH2:14][O:22][C:23]2[C:31]3[N:30]=[C:29]([CH2:32][CH3:33])[N:28]([CH2:70][C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=4)[C:27]=3[CH:26]=[CH:25][CH:24]=2)=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[N:5]([CH3:6])[C:3](=[O:4])[CH2:2][NH:1][C:47](=[O:49])[CH2:46][CH2:45][N:42]1[CH2:41][CH2:40][N:39]([C:37]([NH:36][CH3:35])=[O:38])[CH2:44][CH2:43]1

Participants

4

Reactant 3

HCID 611877693-(4-(Methylcarbamoyl)piperazin-1-yl)propanoic acidHCID 667602672-Amino-N-[2,4-dichloro-3-(2-ethyl-1-pyridin-2-ylmethyl-1H-benzoimidazol-4-yloxymethyl)-phenyl]-N-methyl-acetamideHCID 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 680264274-(3-((2-((2,4-dichloro-3-(((2-ethyl-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylpiperazine-1-carboxamide

Procedure

2-Amino-N-[2,4-dichloro-3-(2-ethyl-1-pyridin-2-ylmethyl-1H-benzoimidazol-4-yloxymethyl)-phenyl]-N-methyl-acetamide and 3-(4-(methylcarbamoyl)piperazin-1-yl)propanoic acid were coupled as described for compound 1 above to give 19. MS (APCI) 694 (M+), 1HNMR (400 MHz, MeOD) δ 2.12 (t, 3H), 2.49 (t, 2H), 2.71 (m, 4H), 2.89 (s, 3H), 2.89 (m, 2H), 2.93 (q, 2H), 3.2 (s, 3H), 3.31 (m, 4H), 3.46-3.84 (dd, 3H), 5.55 (m, 4H), 6.93-8.51 (m, 9Har), LCMS 695 (M+1); C34H38Cl2N8O4+1.73 H2O; Calculated: C, 56.69; H, 5.98; N, 15.56. Found: C, 56.69; H, 6.18; N, 15.81.

Sources & evidence

ORD record
ord-e8d983782aad4de58b8045577e466975
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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