HCID 66589115, compound → 4-(4-((1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline

HRID 1093207Notes

Reaction equation

HRID 1093207 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C:20]([F:23])([F:22])[F:21])[N:17]=[CH:18][C:13]3=[C:12]([N:24]3[CH2:29][C@H:28]4[CH2:30][C@@H:25]3[CH2:26][O:27]4)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.O>[C@@H:28]12[CH2:30][C@@H:25]([N:24]([C:12]3[N:11]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=4)[N:15]=[C:14]4[N:16]([CH2:19][C:20]([F:22])([F:23])[F:21])[N:17]=[CH:18][C:13]=34)[CH2:29]1)[CH2:26][O:27]2

Participants

4

Reactant 1

HCID 66589115HCID 66589115, compound

Product 1

HCID 665890464-(4-((1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)anilineYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (1R,4R)-5-(6-(4-nitrophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (0.50 g, 1.2 mmol) in tetrahydrofuran (20 mL) and water (5 mL) was degassed by the addition of crushed dry ice and then treated with 10% palladium on carbon (50 mg). The resulting suspension was evacuated under weak vacuum and then filled with hydrogen gas (balloon). This evacuation/fill cycle was performed three more times and on the final iteration, the mixture was left to stir overnight under a hydrogen filled balloon. The mixture was filtered through a pad of diatomaceous earth, eluting with methanol. The filtrate was concentrated under reduced pressure to afford 4-(4-((1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline as a gray foam (0.44 g, 93%). MS (ES+): 391.2 (M+H)+

Workup

  1. customwas degassed by the addition of crushed dry ice
  2. additiontreated with 10% palladium on carbon (50 mg)
  3. customThe resulting suspension was evacuated under weak vacuum
  4. additionfilled with hydrogen gas (balloon)
  5. waiton the final iteration, the mixture was left
  6. filtrationThe mixture was filtered through a pad of diatomaceous earth
  7. washeluting with methanol
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7cc40e2edb614b2290010bdb7f95272b
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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