HCID 66589070, compound → tert-butyl 7-(6-(4-aminophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

HRID 1093199Notes

Reaction equation

HRID 1093199 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[CH2:31][CH:30]4[O:32][CH:26]([CH2:27][N:28]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]4)[CH2:25]3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C:20]([F:22])([F:23])[F:21])[N:17]=[CH:18][C:13]3=[C:12]([N:24]3[CH2:31][CH:30]4[O:32][CH:26]([CH2:27][N:28]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]4)[CH2:25]3)[N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 66589070HCID 66589070, compound

Product 1

HCID 66589151tert-butyl 7-(6-(4-aminophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylateYield 94.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of tert-butyl 7-(6-(4-nitrophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (0.54 g, 0.98 mmol) in tetrahydrofuran (10 mL) and ethanol (10 mL) was degassed by the addition of crushed dry ice and then treated with 10% palladium on carbon (30 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 ethanol. The filtrate was concentrated under reduced pressure to afford tert-butyl 7-(6-(4-aminophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate as a white solid (0.48 g, 94%). MS (ES+): 520.2 (M+H)+

Workup

  1. customwas degassed by the addition of crushed dry ice
  2. additiontreated with 10% palladium on carbon (30 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 ethanol
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-260f67eea4134da4802c6f779dd410b2
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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