Hydrochloric Acid → HCID 86707387, compound

HRID 878751Notes

Reaction equation

HRID 878751 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[N:14]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=1)[S:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(=[O:17])=[O:16])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>C(O)C>[OH:3][CH:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[N:14]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:32][CH:33]=1)[S:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 68289639HCID 68289639, compound

Product 1

HCID 86707387HCID 86707387, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-({(4-acetylisoquinolin-3-yl)[4-(trifluoromethoxy)benzyl]amino}-sulfonyl)benzoic acid (20.0 mg, 0.036 mmol) prepared in Example 112 in ethanol (1 mL) was added sodium borohydride (10.0 mg, 0.264 mmol), and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added 1 mol/L hydrochloric acid. The reaction solution was concentrated under reduced pressure, and then diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give 4-({[4-(1-hydroxyethyl)isoquinolin-3-yl][4-(trifluoromethoxy)benzyl]amino}sulfonyl)benzoic acid (17.1 mg, 87%) as a white powder.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record
ord-a42ad631b8de4ea494d08fd451e58f18
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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