Hydrochloric Acid → HCID 86677704, compound

HRID 1499772Notes

Reaction equation

HRID 1499772 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[C:15]([O:36][CH2:37][CH3:38])=[C:16]([CH:22]4[CH2:25][N:24](C(OCC5C=CC=CC=5)=O)[CH2:23]4)[C:17]([CH3:21])=[C:18]([Cl:20])[CH:19]=3)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12.Cl.O>CO.[Pd]>[NH:24]1[CH2:23][CH:22]([C:16]2[C:15]([O:36][CH2:37][CH3:38])=[C:14]([CH:12]([N:8]3[C:4]4=[N:5][CH:6]=[N:7][C:2]([NH2:1])=[C:3]4[C:10]([CH3:11])=[N:9]3)[CH3:13])[CH:19]=[C:18]([Cl:20])[C:17]=2[CH3:21])[CH2:25]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86677703Benzyl 3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}azetidine-1-carboxylate

Product 1

HCID 86677704HCID 86677704, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}azetidine-1-carboxylate (170 mg, 0.32 mmol, racemic intermediate) and 5% palladium (80 mg) were combined in methanol (12 mL), to which was added 0.25 M hydrogen chloride in water (3.2 mL, 0.79 mmol). The suspension was hydrogenated under balloon pressure of H2 at room temperature for 2 h. The suspension was filtered. The filtrate was neutralized with sat. NaHCO3 solution, and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and filtered, concentrated to give the desired product (117 mg, 92%). LCMS calculated for C20H26ClN6O (M+H)+: m/z=401.2; Found: 401.1.

Workup

  1. filtrationThe suspension was filtered
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-174fb0e2cf7c40bc8e1923a70ecffab9
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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