Sodium borohydride → HCID 69521947, compound

HRID 856479Notes

Reaction equation

HRID 856479 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24](C(=O)C(F)(F)F)[CH2:23][CH2:22][C:21]([C:31]([NH:33][C:34]4[CH:39]=[CH:38][C:37]([CH2:40][S:41]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][N+:45]=5[O-:50])(=[O:43])=[O:42])=[CH:36][CH:35]=4)=[O:32])=[CH:20][C:19]=3[CH:51]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>C(O)C>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[NH:24][CH2:23][CH2:22][C:21]([C:31]([NH:33][C:34]4[CH:39]=[CH:38][C:37]([CH2:40][S:41]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][N+:45]=5[O-:50])(=[O:42])=[O:43])=[CH:36][CH:35]=4)=[O:32])=[CH:20][C:19]=3[CH:51]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86595183HCID 86595183, compound

Product 1

HCID 69521947HCID 69521947, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[(1-oxido-2-pyridinyl)sulfonyl]methyl]phenyl]-1-(trifluoroacetyl)-2,3-dihydro-1-benzazepine-4-carboxamide (137 mg) was dissoved in ethanol (4.0 ml), sodium borohydride (36 mg) was added to the mixture, and the mixture was stirred at room temperature for 3 hours. Sodium borohydride (36 mg) was further added to the mixture, and the mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the obtained residue was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[(1-oxido-2-pyridinyl)sulfonyl]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 202) (85 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. additionthe obtained residue was added to water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8827b8a644724baa963296a0e6fe1ed0
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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