Ethyl Acetate → (R)-1-[2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-(pyridin-3-yl)-piperidine-4-carboxylic acid 4-methylpiperazine-amide

HRID 400082Notes

Reaction equation

HRID 400082 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:6]([N:8]1[CH2:12][CH2:11][C@@:10]([CH2:21][CH2:22]CS([O-])(=O)=O)([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:9]1)=[O:7].[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:42]([NH2:44])=[O:43])[CH2:38][CH2:37]1.[N:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:51]2([C:57]([OH:59])=[O:58])[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)[CH:46]=1.C(OCC)(=O)C>CO.ClCCl>[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:42]([NH2:44])=[O:43])[CH2:38][CH2:37]1.[Cl:20][C:15]1[CH:14]=[C:13]([C@@:10]2([CH2:21][CH2:22][N:54]3[CH2:53][CH2:52][C:51]([C:47]4[CH:46]=[N:45][CH:50]=[CH:49][CH:48]=4)([C:57]([OH:59])=[O:58])[CH2:56][CH2:55]3)[CH2:11][CH2:12][N:8]([C:6](=[O:7])[C:5]3[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 676480994-(Pyridin-3-yl)-piperidine-4-carboxylic acid 4-methylpiperazine-amideHCID 86753250(S)-2-[1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate

Product 1

HCID 86753264(R)-1-[2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-(pyridin-3-yl)-piperidine-4-carboxylic acid 4-methylpiperazine-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent5×

Procedure

Prepare by the method of Example 88.6 using (S)-2-[1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate and 4-(pyridin-3-yl)-piperidine-4-carboxylic acid 4-methylpiperazine-amide to give, after chromatography on silica gel eluting sequentially with ethyl acetate, 1% methanol/dichloromethane, 3% methanol/dichloromethane, 5% methanol/dichloromethane, 7% methanol/dichloromethane, and then 9% methanol/dichloromethane, the title compound: Rf =0.29 (silica gel, methanol/dichloromethane/concentrated ammonia 10/90/0.5).

Workup

  1. customto give

Sources & evidence

ORD record
ord-9b7f4da3389341b2b8e514cc7e6bf0da
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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