Avatrombopag Impurity 22 → HCID 87588882, compound

HRID 1869584Notes

Reaction equation

HRID 1869584 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19](=[O:44])[NH:20][C:21]3[S:22][C:23]([N:32]4[CH2:37][CH2:36][N:35]([CH:38]5[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]5)[CH2:34][CH2:33]4)=[C:24]([C:26]4[S:27][CH:28]=[C:29]([Cl:31])[CH:30]=4)[N:25]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C>CO.[OH-].[Na+]>[ClH:18].[Cl:18][C:17]1[C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[N:13][CH:14]=[C:15]([C:19](=[O:44])[NH:20][C:21]2[S:22][C:23]([N:32]3[CH2:37][CH2:36][N:35]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:34][CH2:33]3)=[C:24]([C:26]3[S:27][CH:28]=[C:29]([Cl:31])[CH:30]=3)[N:25]=2)[CH:16]=1

Participants

4

Reactant 1

HCID 87436416Avatrombopag Impurity 22

Product 1

HCID 87588882HCID 87588882, compoundYield 131.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 30 mg of the compound of Example 13 in 1 ml of MeOH, 0.12 ml of 1M NaOH aq. was added at room temperature, and the mixture was stirred for 24 hours. After the solvent was evaporated under reduced pressure, the obtained residue was dissolved in 5 ml of EtOAc, 0.2 ml of 1M HCl was added thereto, and the mixture was stirred for a while. Then, the solvent was evaporated under reduced pressure and washed with diethylether to obtain 20 mg of 1-(3-chloro-5-{[4-(4-chlorothiophen-2-yl)-5-(4-cyclohexylpiperazin-1-yl)thiazol-2-yl]carbamoyl}pyridin-2-yl)piperidine-4-carboxylic acid hydrochloride.

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in 5 ml of EtOAc
  3. addition0.2 ml of 1M HCl was added
  4. stirringthe mixture was stirred for a while
  5. customThen, the solvent was evaporated under reduced pressure
  6. washwashed with diethylether

Sources & evidence

ORD record
ord-0bd7f87d961c4d96aa0a222e0ab16f86
Source dataset
uspto-grants-2009_12
Patent number
US07638536B2

Reaction notes

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