Piperazine → 3-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-piperazin-1-ylmethyl-benzoyloxymethyl ester dihydrochloride salt

HRID 1384508Notes

Reaction equation

HRID 1384508 reaction equation
[CH:1]([C:3]1[CH:52]=[CH:51][C:6]([C:7]([O:9][CH2:10][O:11][C:12]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][C:24]([NH:37][C:38]([O:40][CH2:41][C:42]3[O:43][C:44]4[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=4[CH:46]=3)=[O:39])([C:26](=[O:36])[NH:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])[CH3:25])=[CH:15]2)=[O:13])=[O:8])=[CH:5][CH:4]=1)=O.[NH:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.C(Cl)(Cl)[Cl:60]>>[ClH:60].[ClH:60].[N:53]1([CH2:1][C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][O:11][C:12]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]([CH2:23][C:24]([NH:37][C:38]([O:40][CH2:41][C:42]4[O:43][C:44]5[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=5[CH:46]=4)=[O:39])([C:26](=[O:36])[NH:27][CH:28]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH3:29])[CH3:25])=[CH:15]3)=[O:13])=[O:8])=[CH:51][CH:52]=2)[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 6212ChloroformHCID 206699173-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-formylbenzoyloxymethyl ester

Product 1

HCID 702051293-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-piperazin-1-ylmethyl-benzoyloxymethyl ester dihydrochloride saltYield 43%

Procedure

NaHB(OAc)3 (42 mg, 0.2 mmol, 1.4 eq.) was added to a solution of compound 19 (0.1 g, 0.14 mmol) and piperazine (0.074 g, 0.85 mmol, 6 eq.) in dry chloroform (5 mL) under N2 in an ice bath and stirred 10 minutes. The reaction mixture stirred at room temperature for 19 hours. The reaction was worked up and purified similar as above to give compound 20e as a white foam (47.3 mg, 43%).

Workup

  1. stirringThe reaction mixture stirred at room temperature for 19 hours
  2. custompurified similar as above

Sources & evidence

ORD record
ord-7a62775200b44385b9b9cd002aded4d5
Source dataset
uspto-grants-2001_07
Patent number
US06258800B1

Reaction notes

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