HCID 11685245, compound → HCID 69491173, compound

HRID 852011Notes

Reaction equation

HRID 852011 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:12]2[CH2:18][CH:17]([C:19]([F:22])([F:21])[F:20])[CH2:16][CH2:15][NH:14][C:13]2=[O:23])=[C:6]([F:34])[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][C:6]=2[F:34])[CH:12]2[CH2:18][CH:17]([C:19]([F:21])([F:22])[F:20])[CH2:16][CH2:15][NH:14][C:13]2=[O:23])(=[O:26])=[O:25])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 11685245HCID 11685245, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 69491173HCID 69491173, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-{[(4-Chloro-benzenesulfonyl)-(2-oxo-5-trifluoromethyl-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid methyl ester (0.05 g, 0.09 mmol) in THF (1 ml) was added dropwise to a cooled (ice-bath) suspension of LiAlH4 (0.02 g, 0.44 mmol) in THF (1 ml) under an argon atmosphere. The cold bath was removed and the reaction mixture was further stirred for 3.5 h. Ethyl acetate and a KHSO4/K2SO4 buffer was added to the reaction mixture. The organic fraction was further washed with a KHSO4/K2SO4 (2×), water, brine, dried (Na2 SO4), filtered, concentrated under reduced pressure and purified using preparative RP(C18) chromatography to give 4-chloro-N-(2-fluoro-4-hydroxymethyl-benzyl)-N-(2-oxo-5-trifluoromethyl-azepan-3-yl)-benzenesulfonamide as a lyophilisate: 13 mg; MS: m/e=509.4 (MH+).

Workup

  1. temperaturea cooled
  2. customThe cold bath was removed
  3. additionEthyl acetate and a KHSO4/K2SO4 buffer was added to the reaction mixture
  4. washThe organic fraction was further washed with a KHSO4/K2SO4 (2×), water, brine
  5. customdried (Na2 SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified

Sources & evidence

ORD record
ord-4d2affa705354347856baf707df43e4e
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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