Diisobutylaluminum hydride → HCID 136140517, compound

HRID 1594401Notes

Reaction equation

HRID 1594401 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2=[N:8][NH:9][C:10]([CH:11]3[CH2:14][CH:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[C:18]#N)[CH2:12]3)=[C:5]2[CH:4]([C:23]2[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=2[F:31])[CH2:3]1.CC(C)=[O:34].C(=O)=O.CC(C[AlH]CC(C)C)C>C(Cl)(Cl)Cl>[O:1]=[C:2]1[NH:7][C:6]2=[N:8][NH:9][C:10]([CH:11]3[CH2:12][CH:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[CH:18]=[O:34])[CH2:14]3)=[C:5]2[CH:4]([C:23]2[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=2[F:31])[CH2:3]1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 18522661Acetone cardiceHCID 136140516HCID 136140516, compound

Product 1

HCID 136140517HCID 136140517, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 3-{3-[6-oxo-4-(2,4,5-trifluoro-phenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]-cyclobutyl}-benzonitrile (0.16 g, 0.34 mmol) in CHCl3 (5 mL) at −78° C. (acetone/CO2 bath) was added a solution of DIBAL-H (1.8 mL, 1M in CH2Cl2). After 30 min, the reaction was quenched cold with MeOH (1 mL), followed by a saturated aqueous solution of sodium and potassium tartrates. The reaction mixture was allowed to warm to room temperature and stirred for one hr. The reaction mixture was extracted with CHCl3, and the combined organic layers were dried over MgSO4. The organic layer was filtered, and concentrated under reduced pressure. Purification of this material was accomplished by MPLC using a 10 g ISCO column, eluting with 4% MeOH/CHCl3. The product-containing fractions were collected and concentrated to give the title compound. LRMS m/z (APCI+) 426 (M+1)

Workup

  1. customthe reaction was quenched cold with MeOH (1 mL)
  2. extractionThe reaction mixture was extracted with CHCl3
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationThe organic layer was filtered
  5. concentrationconcentrated under reduced pressure
  6. customPurification of this material
  7. washeluting with 4% MeOH/CHCl3
  8. customThe product-containing fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1f30a571a0af44d5921155e32f8334aa
Source dataset
uspto-grants-2007_11
Patent number
US07300944B2

Reaction notes

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