Sodium borohydride → HCID 69521213, compound

HRID 856480Notes

Reaction equation

HRID 856480 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:43])=[O:42])=[CH:36][CH:35]=4)=[O:32])=[CH:20][C:19]=3[CH:50]=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:35]=[CH:36][C:37]([CH2:40][S:41]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=5)(=[O:43])=[O:42])=[CH:38][CH:39]=4)=[O:32])=[CH:20][C:19]=3[CH:50]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86595184HCID 86595184, compound

Product 1

HCID 69521213HCID 69521213, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (4.9 ml) was dissolved 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[(2-pyridinylsulfonyl)methyl]phenyl]-1-(trifluoroacetyl)-2,3-dihydro-1-benzazepine-4-carboxamide (49 mg), and sodium borohydride (13 mg) was added to the mixture, and the mixture was stirred at room temperature for 3 hours. Sodium borohydride (13 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-[(2-pyridinylsulfonyl)methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 204) (23 mg).

Workup

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

Sources & evidence

ORD record
ord-1ad60d4f5fe44358b6981b31bdfee889
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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