Water → HCID 11371439, compound

HRID 1633729Notes

Reaction equation

HRID 1633729 reaction equation
[CH2:1]([NH:8][C:9]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][C:14]2=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>ClCCl>[CH2:1]([N:8]([C:9]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14](=[O:20])[C:15]=2[C:16]([F:19])=[CH:17][CH:18]=1)[S:28]([CH3:27])(=[O:30])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 11471190HCID 11471190, compound

Product 1

HCID 11371439HCID 11371439, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 44C (0.40 g, 1.5 mmol) in dichloromethane (9 mL) was treated with pyridine (0.36 mL, 4.4 mmol), treated with methanesulfonyl chloride (0.13 mL, 1.6 mmol), stirred for 4 hours, treated with pyridine (0.2 mL, 2.5 mmol), treated with methanesulfonyl chloride (0.10 mL, 1.3 mmol), stirred for 16 hours,refluxed for 9 hours, cooled to ambient temperature, treated with water (25 mL) and extracted with dichloromethane (3×20 mL). The combined dichloromethane extracts were washed with brine, dried (Na2SO4) and concentrated. Purification of the residue on silica gel with 1:1 ethyl acetate:hexanes provided the desired product.

Workup

  1. stirringstirred for 16 hours
  2. temperaturerefluxed for 9 hours
  3. extractionextracted with dichloromethane (3×20 mL)
  4. washThe combined dichloromethane extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification of the residue on silica gel with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-5d2b64c3fbae4fbd970760d9f4eeb4cb
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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