Pyridine → HCID 53238437, compound

HRID 1187306Notes

Reaction equation

HRID 1187306 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[C:4]([C:9]([C:11]2[C:19]3[C:18]([O:20][CH3:21])=[N:17][CH:16]=[N:15][C:14]=3[NH:13][CH:12]=2)=[O:10])[C:5]([F:8])=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH2:29]([C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1)[CH3:30]>O1CCCC1>[F:22][C:3]1[C:4]([C:9]([C:11]2[C:19]3[C:18]([O:20][CH3:21])=[N:17][CH:16]=[N:15][C:14]=3[NH:13][CH:12]=2)=[O:10])=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH:1][S:37]([C:34]1[CH:35]=[CH:36][C:31]([CH2:29][CH3:30])=[CH:32][CH:33]=1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5709594-Ethylbenzene-1-sulfonyl chlorideHCID 57963243HCID 57963243, compound

Product 1

HCID 53238437HCID 53238437, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (3-amino-2,6-difluoro-phenyl)-(4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (36, 30.0 mg, 0.0986 mmol) 1.0 mL of tetrahydrofuran and pyridine (23.9 μL, 0.296 mmol) are added, followed by 4-ethyl-benzenesulfonyl chloride (59, 40.4 mg, 0.197 mmol). The reaction vial is stirred at room temperature for 5 days, then extracted by adding aqueous saturated sodium chloride and ethyl acetate. The organic layer is washed with water, then sodium bicarbonate, then brine, and dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-1008, 27 mg). MS (ESI) [M+H+]+=473.0.

Workup

  1. customThe reaction
  2. extractionextracted
  3. additionby adding aqueous saturated sodium chloride and ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialsodium bicarbonate, then brine, and dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material is purified by silica gel column chromatography
  9. washeluting with ethyl acetate and hexane
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3fafed01ad7e42f4a52ab3fd95edfabe
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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