Hydrochloric Acid → HCID 22903535, compound

HRID 1489084Notes

Reaction equation

HRID 1489084 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:37])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:36])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][CH2:30][C:31](OCC)=[O:32])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:38]=1.CO[BH-](OC)OC.[Na+].Cl>COCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:37])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:36])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3084262Sodium hydrido[tris(methanolato)]borate(1-)HCID 22903504HCID 22903504, compound

Product 1

HCID 22903535HCID 22903535, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 7-chloro-1-{6-[2-(3-ethoxycarbonylpropoxy)benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (2.5 g) in ethylene glycol dimethyl ether (70 ml) is added sodium trimethoxyborohydride (3.78 g), and the mixture is refluxed for 3 hours. The reaction solution is gradually poured into diluted hydrochloric acid, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography, and recrystallized from dichloromethane-diethyl ether to give 7-chloro-1-{6-[2-(4-hydroxybutoxy)benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (1.12 g) as white powder.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography
  8. customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-bc9b3b8aed2e417c8fd4dbd4636f0add
Source dataset
uspto-grants-1997_10
Patent number
US05677299

Reaction notes

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