Pyridine → HCID 68901099, compound

HRID 2122046Notes

Reaction equation

HRID 2122046 reaction equation
N1C=CC=CC=1.[CH3:7][N:8]([CH:18]1[CH:23]([CH3:24])[CH2:22][CH2:21][NH:20][CH2:19]1)[C:9]1[C:10]2[CH:17]=[CH:16][NH:15][C:11]=2[N:12]=[CH:13][N:14]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>ClCCl>[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([N:20]2[CH2:21][CH2:22][CH:23]([CH3:24])[CH:18]([N:8]([CH3:7])[C:9]3[C:10]4[CH:17]=[CH:16][NH:15][C:11]=4[N:12]=[CH:13][N:14]=3)[CH2:19]2)(=[O:35])=[O:34])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 12084830N-Methyl-N-[(3S,4S)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 68901099HCID 68901099, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1 mL of pyridine and 9 ml of dichloromethane was added 40 mg (0.163 mmol) of the product from Method H and 20 L of 4-methoxy-benzenesulfonyl chloride and the resulting mixture stirred at room temperature for 18 hours. The reaction was then quenched upon addition of saturated NaHCO3 (aq), the organic layer was removed and the aqueous layer extracted with dichloromethane. The dichloromethane layer was dried over Na2SO4 and concentrated to dryness in vacuo. The residue was purified by PTLC (silica; 10:1 dichloromethane/methanol) affording 22 mg (32%) of the title compound as a light yellow solid. LRMS: 416.5 (M+1).

Workup

  1. customThe reaction was then quenched upon addition of saturated NaHCO3 (aq)
  2. customthe organic layer was removed
  3. extractionthe aqueous layer extracted with dichloromethane
  4. dry with materialThe dichloromethane layer was dried over Na2SO4
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue was purified by PTLC (silica; 10:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-484f3b143e964aa297ff672887914538
Source dataset
uspto-grants-2004_02
Patent number
US06696567B2

Reaction notes

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