Hydrochloric Acid → 6-(1-(azetidin-3-yl)piperidin-3-yl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrochloride

HRID 68726Notes

Reaction equation

HRID 68726 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([CH:12]3[CH2:17][CH2:16][CH2:15][N:14]([CH:18]4[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]4)[CH2:13]3)=[N:6][C:5]=2[N:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:3]=1.[ClH:35]>>[ClH:35].[NH:20]1[CH2:21][CH:18]([N:14]2[CH2:15][CH2:16][CH2:17][CH:12]([C:7]3[NH:8][C:9](=[O:11])[C:10]4[C:2]([CH3:1])=[N:3][N:4]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:5]=4[N:6]=3)[CH2:13]2)[CH2:19]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 136386278tert-butyl 3-(3-(3-methyl-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)piperidin-1-yl)azetidine-1-carboxylate

Product 1

HCID 1363862796-(1-(azetidin-3-yl)piperidin-3-yl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrochloride

Procedure

Into a 100-mL round-bottom flask, was placed a solution of tert-butyl 3-(3-(3-methyl-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)piperidin-1-yl)azetidine-1-carboxylate (200 mg, 0.43 mmol, 1.00 equiv) in hydrogen chloride (5 mL) at room temperature. The resulting solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum. The resulting residue (150 mg) was purified by Prep-HPLC with the following conditions (Gilson Pre-HPLC): Column, SHISEIDO, CAPCELL PAK C18, 20 mm ID*250 mm, 5 u; mobile phase, methanol/H2O; Detector, UV 254 nm to yield 6-(1-(azetidin-3-yl)piperidin-3-yl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrochloride as a white solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customat room temperature
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux overnight
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThe resulting residue (150 mg) was purified by Prep-HPLC with the following conditions (Gilson Pre-HPLC)

Sources & evidence

ORD record
ord-ec50c70e4e5540698c9be724c786e5a0
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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