Trifluoroacetic acid methylene chloride → 4-(4-ethoxy-2-fluoro-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt

HRID 1931602Notes

Reaction equation

HRID 1931602 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][C:25]=4[F:33])=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].ClCCl>>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[CH2:31]([O:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][C:22]2[N:21]=[CH:20][N:19]=[C:18]3[N:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[N:15]=[CH:16][C:17]=23)=[C:25]([F:33])[CH:26]=1)[CH3:32]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 445141064-[4-(4-Ethoxy-2-fluoro-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 669153124-(4-ethoxy-2-fluoro-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate saltYield 99%

Procedure

A solution of 4-[4-(4-ethoxy-2-fluoro-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 43; 110 mg) in 20% trifluoroacetic acid/dichloromethane (5 mL) was stirred at room temperature for 3 hours. The solvent was removed to afford 4-(4-ethoxy-2-fluoro-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (112 mg, 99%) which was used directly in the next step without further purification.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-a226d6c655db43f19d421f361f0c086f
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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