Valeryl chloride → HCID 21104422, compound

HRID 1354178Notes

Reaction equation

HRID 1354178 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[C:40](Cl)(=[O:45])[CH2:41][CH2:42][CH2:43][CH3:44]>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH:30][C:40](=[O:45])[CH2:41][CH2:42][CH2:43][CH3:44])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:17])([F:18])[F:19])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 61186Valeryl chlorideHCID 81531DiisopropylethylamineHCID 9845828HCID 9845828, compound

Product 1

HCID 21104422HCID 21104422, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 4-[2-(3-fluoro-phenyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridin-3-yl]benzenesulfonamide (0.109 g 0.25 mmol) in chloroform (10 ml) was added diisopropylethylamine (Aldrich) (100 μl), 4-dimethylaminopyridine (0.02 g 0.16 mmol) and valeryl chloride (Aldrich) (0.072 g 0.6 mmol) and the reaction was stirred at room temperature for 20 hr. It was washed with M Na2CO3 (5 ml), water (5 ml) and dried (MgSO4). Removal of solvent gave a solid which was purified by SPE chromatography. Elution with cyclohexane:ethyl acetate (2:1) gave the title compound as a white solid (0.075 g 58%).

Workup

  1. washIt was washed with M Na2CO3 (5 ml), water (5 ml)
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvent
  4. customgave a solid which
  5. customwas purified by SPE chromatography
  6. washElution with cyclohexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-1ff55d350ea94089b7f88a2c8215cf07
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

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