HCID 66588996, compound → 4-(4-((1S,4S)-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 1093203Notes

Reaction equation

HRID 1093203 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.C(OCC)(=O)C>[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 66588996HCID 66588996, compound

Product 1

HCID 665890974-(4-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (1S,4S)-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 (0.84 mmol maximum) in tetrahydrofuran (15 mL) and ethyl acetate (15 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-((1S,4S)-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 white foam (0.26 g, 78% over 2 steps). MS (ES+): 391.1 (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-5c9c6cdde50f44be8e34631c3dbbce61
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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