Hydrochloric Acid → HCID 46189904, compound

HRID 2360528Notes

Reaction equation

HRID 2360528 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[C:8]([O:47][CH3:48])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:46])[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](=[O:45])[CH2:31][N:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>ClCCl.C(O)(C)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:49][S:50]([CH3:53])(=[O:51])=[O:52])[C:8]([O:47][CH3:48])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:46])[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](=[O:45])[CH2:31][N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH2:28][CH2:29]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 58493972HCID 58493972, compound

Product 1

HCID 46189904HCID 46189904, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

160 mg tert-butyl 4-(2-{4-[2-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylcarbamoyl)-1-methyl-1H-indol-7-ylmethyl]-piperazin-1-yl}-2-oxo-ethyl)-piperazine-1-carboxylate are dissolved in 5 ml dichloromethane, combined with 1 ml of a 5 M solution of hydrogen chloride in isopropanol and stirred for 12 hours at ambient temperature. Then the solvents are eliminated in vacuo and the residue is divided between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution and then dried on magnesium sulphate. The solvent is eliminated in vacuo and the residue is chromatographed on aluminium oxide (dichloromethane/methanol 100:0 to 95:5).

Workup

  1. washThe organic phase is washed with saturated aqueous sodium chloride solution
  2. customdried on magnesium sulphate
  3. customthe residue is chromatographed on aluminium oxide (dichloromethane/methanol 100:0 to 95:5)

Sources & evidence

ORD record
ord-50ad57102cd9490697edbf2d930cc1f8
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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