Methanol → N-(2-Phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl)benzenesulfonamide

HRID 901217Notes

Reaction equation

HRID 901217 reaction equation
[C:1]1([N:7]2[CH:15]=[C:14]3[C:9]([N:10]=[CH:11][C:12]([NH:16][S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])=[CH:13]3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>CCOC(C)=O.[OH-].[Pd+2].[OH-]>[C:1]1([N:7]2[CH:15]=[C:14]3[C:9]([NH:10][CH2:11][CH:12]([NH:16][S:17]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)(=[O:18])=[O:19])[CH2:13]3)=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 58670149N-(2-Phenyl-2H-pyrazolo[3,4-b]pyridin-5-yl)benzenesulfonamide

Product 1

HCID 135983736N-(2-Phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3D (50 mg, 0.142 mmol) and palladium hydroxide (20% wt of Pd) on carbon (50 mg) in EtOAc (5 mL)/methanol(2 mL) was stirred under a hydrogen balloon for 5 hours, then filtered via a pad of Celite. The filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with 2.0 M NH3 in MeOH/CH2Cl2 (3:97 ratio) to give the desired product, which was further purified using preparative HPLC to give the title compound as a TFA salt (15 mg, 22% yield). LC/MS (method A): retention time=2.75 min, (M+H)+=355.

Workup

  1. filtrationfiltered via a pad of Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe resultant residue was purified by silica gel column chromatography
  4. washeluting with 2.0 M NH3 in MeOH/CH2Cl2 (3:97 ratio)

Sources & evidence

ORD record
ord-c7acbd60e99a467e97c201a9178a3527
Source dataset
uspto-grants-2008_04
Patent number
US07361766B2

Reaction notes

Loading…