1-Methylpiperazine → HCID 46189950, compound

HRID 2360529Notes

Reaction equation

HRID 2360529 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:41]=O)[C:8]([O:39][CH3:40])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:38])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]([C@@H:32]3[CH2:36][CH2:35][CH2:34][N:33]3[CH3:37])=[O:31])[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:43][N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.ClCCl.C(O)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH2:41][N:47]2[CH2:48][CH2:49][N:44]([CH3:43])[CH2:45][CH2:46]2)[C:8]([O:39][CH3:40])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:38])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][N:24]2[CH2:25][CH2:26][N:27]([C:30]([C@@H:32]3[CH2:36][CH2:35][CH2:34][N:33]3[CH3:37])=[O:31])[CH2:28][CH2:29]2)=[O:13])[CH:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58493994HCID 58493994, compound

Product 1

HCID 46189950HCID 46189950, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

160 mg of (S)-1-methyl-7-[4-(1-methyl-pyrrolidine-2-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid-(5-tert-butyl-3-formyl-2-methoxy-phenyl)-amide are dissolved in 2 ml of 1,2-dichloroethane, combined successively with 40 μl acetic acid and 45 μl of 1-methylpiperazine and stirred for 1 hour at ambient temperature. Then 70 mg of sodium triacetoxyborohydride are added and the mixture is stirred for 5 hours. Then it is divided between dichloromethane and saturated aqueous sodium hydrogen carbonate solution and the organic phase is washed with saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is purified by preparative HPLC (method 7).

Workup

  1. stirringthe mixture is stirred for 5 hours
  2. washthe organic phase is washed with saturated aqueous sodium chloride solution
  3. dry with materialAfter drying with magnesium sulphate the solvents
  4. customthe residue is purified by preparative HPLC (method 7)

Sources & evidence

ORD record
ord-9bd906dede374bdcba66dc82662246c0
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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