Water → HCID 89962611, compound

HRID 337874Notes

Reaction equation

HRID 337874 reaction equation
[NH2:1][C:2]1[C:6]([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2[O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([S:21]([N:24]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][C:33]=3[O:40][CH3:41])[C:25]3[CH:30]=[CH:29][N:28]=[CH:27][N:26]=3)(=[O:23])=[O:22])=[C:16]([F:42])[CH:15]=2)=[CH:5][N:4]([CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][O:44]2)[N:3]=1.[C:49](OC(=O)C)(=[O:51])[CH3:50].O.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:41][O:40][C:33]1[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=[CH:37][C:32]=1[CH2:31][N:24]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][N:26]=1)[S:21]([C:17]1[C:16]([F:42])=[CH:15][C:14]([O:13][C@H:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@@H:7]2[C:6]2[C:2]([NH:1][C:49](=[O:51])[CH3:50])=[N:3][N:4]([CH:43]3[CH2:48][CH2:47][CH2:46][CH2:45][O:44]3)[CH:5]=2)=[C:19]([CH3:20])[CH:18]=1)(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 89963035HCID 89963035, compound

Product 1

HCID 89962611HCID 89962611, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the 4-({(1S*,2R*)-2-[3-amino-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]cyclohexyl}oxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-5-methyl-N-(pyrimidin-4-yl)benzenesulfonamide (78 mg, 0.115 mmol) prepared in Example 96a in pyridine (0.50 mL), acetic anhydride (0.021 mL, 0.229 mmol) was added, and the reaction solution was stirred at room temperature for 12 hours. To the reaction solution, water (10 mL) and ethyl acetate (10 mL) were added, and the organic layer was washed with water (10 mL) and then saturated saline (10 mL) and dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography to yield the title compound (37.2 mg, 45%) as a colorless amorphous solid.

Workup

  1. washthe organic layer was washed with water (10 mL)
  2. dry with materialsaturated saline (10 mL) and dried over anhydrous sodium sulfate
  3. concentrationAfter vacuum concentration
  4. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-09409e7550fc44b7b784aa4c098f86ac
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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