Hydrochloric Acid → HCID 58493931, compound

HRID 2360533Notes

Reaction equation

HRID 2360533 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:41][O:42][Si](C)(C)C)[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].Cl.C(=O)([O-])O.[Na+]>ClCCl.C(O)(C)C>[C:1]([C:5]1[CH:6]=[C:7]([CH2:41][OH:42])[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])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58493958HCID 58493958, compound

Product 1

HCID 58493931HCID 58493931, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

270 mg of (S)-1-methyl-7-[4-(1-methyl-pyrrolidine-2-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid-(5-tert-butyl-2-methoxy-3-trimethylsilanyloxymethyl-phenyl)-amide are dissolved in 5 ml dichloromethane, mixed with 833 μl of a 5 M solution of hydrogen chloride in isopropanol and stirred for 30 minutes at ambient temperature. The mixture is divided between dichloromethane and saturated aqueous sodium hydrogen carbonate solution, the aqueous phase is extracted twice with dichloromethane and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the product thus obtained is purified by preparative HPLC (method 3).

Workup

  1. extractionthe aqueous phase is extracted twice with dichloromethane
  2. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  3. dry with materialAfter drying with magnesium sulphate the solvents
  4. customthe product thus obtained
  5. customis purified by preparative HPLC (method 3)

Sources & evidence

ORD record
ord-47456a20a3054a1bb788b302ec362b5d
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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