Hydrogen chloride-ethyl acetate → (S)-N-[2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl]-N-methyl-2-(morpholin-4-yl)propionamide hydrochloride

HRID 2068889Notes

Reaction equation

HRID 2068889 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:10][C:9]2[NH:8][N:7]=[C:6]([C:11]3[NH:12][C:13]4[C:18]([CH:19]=3)=[CH:17][CH:16]=[C:15]([N:20]([CH3:31])[C:21](=[O:30])[C@@H:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH3:23])[CH:14]=4)[C:5]=2[CH2:4][CH2:3]1.[ClH:33].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:33].[CH3:32][C:2]1([CH3:1])[CH2:10][C:9]2[NH:8][N:7]=[C:6]([C:11]3[NH:12][C:13]4[C:18]([CH:19]=3)=[CH:17][CH:16]=[C:15]([N:20]([CH3:31])[C:21](=[O:30])[C@@H:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH3:23])[CH:14]=4)[C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 135980528ITK inhibitor 2

Product 1

HCID 136359922(S)-N-[2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl]-N-methyl-2-(morpholin-4-yl)propionamide hydrochlorideYield 69.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)—N-[2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl]-N-methyl-2-(morpholin-4-yl)propionamide obtained in Example 4 (100 mg, 0.23 mmol) in ethyl acetate (1 ml) was added 4 N hydrochloric acid/ethyl acetate (0.06 ml, 0.24 mmol) at room temperature, and the mixture was stirred for 30 min. The precipitated crystals were collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give the title compound (75 mg, 69%).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with ethyl acetate
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-c5056e6bb69745ddb979789d4fc57d7d
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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