Benzyl chloroformate → HCID 136358105, compound

HRID 456618Notes

Reaction equation

HRID 456618 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[NH:19][N:18]=1>C(N(CC)CC)C.ClCCl>[CH2:5]([O:4][C:2]([N:19]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[C:17]([C:13]2[NH:12][CH:16]=[CH:15][CH:14]=2)=[N:18]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 178420814HCID 178420814, compound

Product 1

HCID 136358105HCID 136358105, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (150 mg) (Aldrich, Milwaukee, Wis.) was added to a mixture of 3-(1H-pyrrol-2-yl)-1H-pyrazolo[3,4-b]pyridine (120 mg) (from Example 2) and triethylamine (3 drops) in dichloromethane (DCM). After stirring at room temperature for one hour, the reaction was concentrated and purified on a silica gel column to give 3-(1H-pyrrol-2-yl)-pyrazolo[3,4-b]pyridine-1-carboxylic acid benzyl ester. It was then combined with di-morpholine methane (300 mg) (Aldrich, Milwaukee, Wis.), THF (2 mL), water (0.2 mL) and acetic acid (2 drops). The mixture was heated at 90° C. for 20 hours. The reaction was concentrated and purified on a silica gel column to give 30 mg of the titled compound as a white solid.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified on a silica gel column

Sources & evidence

ORD record
ord-a98493c1609149d9ba87090025e41fe0
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

Loading…