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Hydrochloric Acid → Btk inhibitor 1 (R enantioMer hydrochloride)

HRID 1485330
Notes
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Reaction equation

HRID 1485330 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)[C:3]=12.[ClH:37]>O1CCOCC1.C(OCC)C>[ClH:37].[O:17]([C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][C:2]=3[NH2:1])[N:8]([C@@H:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)[N:9]=2)=[CH:16][CH:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59799012(R)-tert-Butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 78357770Btk inhibitor 1 (R enantioMer hydrochloride)Yield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31275
1,4-Dioxane
Solvent
3×

Procedure

Compound 35 (700 mg, 1.48 mmol, 1 equiv) was dissolved in dioxane (8 mL). A solution of hydrogen chloride in dioxane (4 mL of a 4 N solution in dioxane, 16 mmol, 10.7 equiv) was added and the reaction was stirred at room temperature overnight. The reaction was diluted with diethyl ether (20 mL) and the resulting solids were collected by filtration under a stream of nitrogen. The product was further dried in a vacuum oven to yield 36 (550 mg, 88% yield) as an off-white solid.

Workup

  1. filtrationthe resulting solids were collected by filtration under a stream of nitrogen
  2. customThe product was further dried in a vacuum oven

Sources & evidence

ORD record
ord-e9c4b178b3cf4752b19cb579fcae36db
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422295B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes