Water → HCID 69057074, compound

HRID 1437644Notes

Reaction equation

HRID 1437644 reaction equation
Cl.[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([F:33])[CH:24]=2)[CH2:19][CH2:18][NH:17][CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].O>C1COCC1.CCN(CC)CC>[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:26]=[C:25]([F:33])[CH:24]=2)[CH2:19][CH2:18][N:17]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 69059221HCID 69059221, compound

Product 1

HCID 69057074HCID 69057074, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of the compound (28.8 mg) obtained in Example 26 in THF (2.0 ml), Et3N (25.1 μl) was added, methylsulfonyl chloride (9.3 μl) was added at 0° C., and the reaction mixture was reacted at room temperature 24 hours. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% citric acid solution and saturated brine, and dried, and the solvent was evaporated under reduced pressure, and then the residue was purified by preparative HPLC to obtain the title compound.

Workup

  1. customthe reaction mixture was reacted at room temperature 24 hours
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous 10% citric acid solution and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2f8305a2e91b420081e6bfde3c05fcaa
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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