HCID 66589006, compound → HCID 66589057, compound

HRID 1093190Notes

Reaction equation

HRID 1093190 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[CH:29]4[CH2:30][CH2:31][CH:25]3[CH2:26][O:27][CH2:28]4)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.C(OCC)(=O)C>[CH:25]12[N:24]([C:12]3[N:11]=[C:10]([C:7]4[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=4)[N:15]=[C:14]4[N:16]([CH2:19][C:20]([F:21])([F:23])[F:22])[N:17]=[CH:18][C:13]=34)[CH:29]([CH2:30][CH2:31]1)[CH2:28][O:27][CH2:26]2

Participants

4

Reactant 1

HCID 66589006HCID 66589006, compound

Product 1

HCID 66589057HCID 66589057, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 8-(6-(4-nitrophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (0.59 g, 1.4 mmol) in tetrahydrofuran (40 mL) and ethyl acetate (10 mL) was degassed by the addition of crushed dry ice and then treated with 10% palladium on carbon (100 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-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline as a white solid (0.51 g, 89%). MS (ES+): 405.0 (M+H)+

Workup

  1. customwas degassed by the addition of crushed dry ice
  2. additiontreated with 10% palladium on carbon (100 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. additionfilled balloon
  7. filtrationThe mixture was filtered through a pad of diatomaceous earth
  8. washeluting with methanol
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b1af319ead4451b9043429609304058
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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