Acetic Anhydride → HCID 89963113, compound

HRID 338024Notes

Reaction equation

HRID 338024 reaction equation
[Cl:1][C:2]1[C:3]([O:19][C@H:20]2[CH2:25][CH2:24][C@@H:23]([OH:26])[CH2:22][C@@H:21]2[C:27]2[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=2)=[CH:4][C:5]([F:18])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:33]([O:26][C@@H:23]1[CH2:24][CH2:25][C@H:20]([O:19][C:3]2[CH:4]=[C:5]([F:18])[C:6]([S:8](=[O:10])(=[O:9])[NH:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][N:13]=3)=[CH:7][C:2]=2[Cl:1])[C@@H:21]([C:27]2[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=2)[CH2:22]1)(=[O:35])[CH3:34]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 89962787HCID 89962787, compound

Product 1

HCID 89963113HCID 89963113, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of the 5-chloro-2-fluoro-4-{[(1S,2R,4R)-4-hydroxy-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide (22.0 mg, 0.046 mmol) prepared in Example 165d, acetic anhydride (0.50 mL) and 4-(N,N-dimethylamino)pyridine (0.6 mg, 0.0046 mmol) in pyridine (1.0 mL) was stirred at room temperature for 3 hours. The reaction solution was concentrated, and 1 M HCl (10 mL) was then added to the residue, followed by extraction with dichloromethane (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (dichloromethane/methanol=10:1) to yield the title compound (22.0 mg, 91%) as a colorless solid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. addition1 M HCl (10 mL) was then added to the residue
  3. extractionfollowed by extraction with dichloromethane (50 mL)
  4. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography (dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-2d51f5313ee846318062b36f3bd0f0cb
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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