Thionyl Chloride → HCID 178449399, compound

HRID 456637Notes

Reaction equation

HRID 456637 reaction equation
C(O[C:4]([C:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[NH:8][CH:7]=1)=[O:5])C.S(Cl)(Cl)=O>>[CH2:7]([NH:8][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[NH:8][CH:7]=1)=[O:5])[CH:6]([CH3:10])[CH3:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178469891HCID 178469891, compound

Product 1

HCID 178449399HCID 178449399, compound

Procedure

A mixture of 5-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (100 mg, 0.44 mmol) (from Example 11) and thionyl chloride (2M in DCM, 5 mL) was heated to reflux for 2 hours. The reaction was concentrated, the residue was then stirred with isobutyl amine (excess) in DCM at room temperature for 2 hours. The reaction was diluted with DCM, washed with water, dried and concentrated. The residue was purified on a silica gel column to give the titled compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated
  4. additionThe reaction was diluted with DCM
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-ee0d7a8dd5e64d23bfad0f6061f48b14
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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