Methanol → HCID 135448247, compound

HRID 1594402Notes

Reaction equation

HRID 1594402 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)[CH:18]=[O:19])[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.CO.[BH4-].[Na+]>C1COCC1>[OH:19][CH2:18][C:17]1[CH:16]=[C:15]([CH:13]2[CH2:12][CH:11]([C:10]3[NH:9][N:8]=[C:6]4[C:5]=3[CH:4]([C:23]3[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=3[F:31])[CH2:3][C:2](=[O:1])[NH:7]4)[CH2:14]2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 136140517HCID 136140517, compound

Product 1

HCID 135448247HCID 135448247, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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}-benzaldehyde (15 mg, 0.03 mmol) in THF:MeOH (3 mL 3:1) was added sodium borohydride (10 mg, 0.26 mmol). After 30 min, the reaction was quenched by the addition of 5 drops of aqueous NaOH (1N). The reaction mixture was concentrated under reduced pressure. Purification of this material was accomplished by preparative plated chromatography. The product band was collected, extracted with EtOAc, filtered, and concentrated to give the title compound. LRMS m/z (APCI+) 428 (M+1).

Workup

  1. customthe reaction was quenched by the addition of 5 drops of aqueous NaOH (1N)
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customPurification of this material
  4. customThe product band was collected
  5. extractionextracted with EtOAc
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-189cb2d699b34d3ea5d4c1854fd23fd3
Source dataset
uspto-grants-2007_11
Patent number
US07300944B2

Reaction notes

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