Water → HCID 67278426, compound

HRID 1696230Notes

Reaction equation

HRID 1696230 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C:9]2[C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=[C:11]3[NH:18][CH:19]=[CH:20][C:10]=23)[CH2:3]1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>ClCCl.C(Cl)(Cl)Cl>[CH3:28][S:29]([N:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C:9]2[C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=[C:11]3[NH:18][CH:19]=[CH:20][C:10]=23)[CH2:3]1)(=[O:31])=[O:30]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67277770HCID 67277770, compound

Product 1

HCID 67278426HCID 67278426, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(3R)-3-piperidinylamino]-1H-pyrrolo[2,3-b]-pyridine-5-carboxamide hydrochloride (50 mg) in dichloromethane (1.0 mL) were added triethylamine (0.014 mL) and methanesulfonyl chloride (0.094 mL) at 4° C. The mixture was stirred at ambient temperature for 5 hours. To the mixture was added water and chloroform and the organic layer was extracted with chloroform. The extract was washed with saturated aqueous sodium hydrogencarbonate, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform and methanol to give 4-{[(3R)-1-(methylsulfonyl)-3-piperidinyl]-amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (7 mg) as a white powder.

Workup

  1. extractionthe organic layer was extracted with chloroform
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel with chloroform and methanol

Sources & evidence

ORD record
ord-8516c203fb984d86b4692704ed08558d
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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