Thionyl Chloride → HCID 178514036, compound

HRID 456643Notes

Reaction equation

HRID 456643 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.Cl.[NH2:25][CH2:26][C:27]([NH2:29])=[O:28]>O>[C:27]([CH2:26][NH:25][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])(=[O:28])[NH2:29]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 2723639Glycinamide hydrochlorideHCID 178469891HCID 178469891, compound

Product 1

HCID 178514036HCID 178514036, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (100 mg, 0.43 mmol) (from Example 11) and thionyl chloride (0.2M in DCM, 10 mL) was heated to reflux for 2 hours. The reaction was concentrated, the residue was dissolved in DCM, to it was added glycinamide hydrochloride (242 mg, 2.19 mmol), followed by TEA. The mixture was then stirred at room temperature until the reaction was completed by TLC. The reaction was diluted with water and extracted with DCM. The combined DCM was concentrated and purified on a silica gel column to give the titled compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated
  4. dissolutionthe residue was dissolved in DCM, to it
  5. extractionextracted with DCM
  6. concentrationThe combined DCM was concentrated
  7. custompurified on a silica gel column

Sources & evidence

ORD record
ord-240fc2eda48341ec89fba7969702d37f
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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