3-(4-Acetyl-piperazin-1-yl)-propionic acid → HCID 66760558, compound

HRID 889185Notes

Reaction equation

HRID 889185 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl: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[Cl:34])[CH3:6])=[O:4].[C:35]([N:38]1[CH2:43][CH2:42][N:41]([CH2:44][CH2:45][C:46](O)=[O:47])[CH2:40][CH2:39]1)(=[O:37])[CH3:36].ClC1C(COC2C3N=C(OC)N(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>>[C:35]([N:38]1[CH2:43][CH2:42][N:41]([CH2:44][CH2:45][C:46]([NH:1][CH2:2][C:3]([N:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([CH2:14][O:15][C:16]3[C:24]4[N:23]=[C:22]([O:25][CH3:26])[N:21]([CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=5)[C:20]=4[CH:19]=[CH:18][CH:17]=3)[C:8]=2[Cl:34])[CH3:6])=[O:4])=[O:47])[CH2:40][CH2:39]1)(=[O:37])[CH3:36]

Participants

4

Reactant 3

HCID 20506993-(4-Acetyl-piperazin-1-yl)-propionic 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 66760558HCID 66760558, compound

Procedure

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 3-(4-acetylpiperazin-1-yl)propanoic acid were used to prepare 16 as described for compound 1. LCMS (+ESI) 668 (M). 1H-NMR (CDCl3, δ): 8.58 (m, 1H), 7.84 (bt, 1H), 7.58 (t, J=2.0 Hz, 1H), 7.47 (d, J=8.8 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.18 (m, 1H), 7.03 (t, J=8.0 Hz, 1H), 6.92 (d, J=8.0 Hz, 1H), 6.82 (m, 2 H), 5.68 (d, J=4.0 Hz, 2H), 5.28 (s, 2H), 4.21 (s, 3H), 3.89 (dd, 1H), 3.69 (m, 2H), 3.25 (s, 3H), 2.53 (m, 4H), 2.04 (s, 3H). Calcd. for C33H37Cl2N7O5+1H2O: C, 56.57; H, 5.61; N, 13.99. Found: C, 56.33; H, 5.48; N, 14.21.

Workup

  1. customto prepare 16

Sources & evidence

ORD record
ord-b469cd6a70e74daab5dc7270457ee33d
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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