Methanol → HCID 58246319, compound

HRID 242097Notes

Reaction equation

HRID 242097 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][CH2:23][NH:24][S:25]([C:28]5[CH:29]=N[N:31]([CH3:33])[CH:32]=5)(=[O:27])=[O:26])[CH:19]=4)[CH2:14][CH2:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].[CH3:36]O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][CH2:23][NH:24][S:25]([C:28]5[CH:32]=[N:31][CH:33]=[CH:36][CH:29]=5)(=[O:27])=[O:26])[CH:19]=4)[CH2:14][CH2:13][NH:12]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 66868661HCID 66868661, compound

Product 1

HCID 58246319HCID 58246319, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-[2-({1-[1-(4-chlorophenyl)cyclopropyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]-1-methyl-1H-pyrazole-4-sulfonamide (46 mg, 0.09 mmol), sodium borohydrid (7.2 mg, 0.19 mmol) in water (0.25 ml) and methanol (2 ml) was stirred for 3 days at room temperature. The solvent was removed, the residue dissolved in methylenehloride and extracted with water. The methylenehloride was evaporated and the remaining solid purified by chromatography. Yield: 20 mg (0.04 mmol, 43%)

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in methylenehloride
  3. extractionextracted with water
  4. customThe methylenehloride was evaporated
  5. customthe remaining solid purified by chromatography

Sources & evidence

ORD record
ord-3cf33c54359d49789b3bcf7c83803529
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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