Water → HCID 59520520, compound

HRID 1162771Notes

Reaction equation

HRID 1162771 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[C:11]([CH:12]=[O:13])=[CH:10][N:9]([CH2:14][C:15]([NH:17][C:18]2[S:22][C:21]3[CH2:23][CH2:24][CH2:25][CH2:26][C:20]=3[C:19]=2[C:27]([NH2:29])=[O:28])=[O:16])[N:8]=1)([CH3:6])([CH3:5])[CH3:4].O>C1COCC1>[C:3]([C:7]1[C:11]([CH2:12][OH:13])=[CH:10][N:9]([CH2:14][C:15]([NH:17][C:18]2[S:22][C:21]3[CH2:23][CH2:24][CH2:25][CH2:26][C:20]=3[C:19]=2[C:27]([NH2:29])=[O:28])=[O:16])[N:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59520484HCID 59520484, compound

Product 1

HCID 59520520HCID 59520520, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (50 mg, 1.3 mmol) was added to a solution of 2-[2-(3-tert-Butyl-4-formylpyrazol-1-yl)-acetylamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxamide (100 mg, 0.25 mmol) in THF (2 mL). The mixture was stirred for 1 h at ambient temperature. Water was added and the product extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography using eluants EtOAc/heptane. The solid isolated was further purified by preparative reverse phase HPLC and passed down an SCX cartridge. The volatiles were blown off with nitrogen to give a white solid (2.4 mg, 0.61 μmol, 2%).

Workup

  1. extractionthe product extracted with EtOAc
  2. dry with materialThe combined organics were dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography
  5. customThe solid isolated
  6. customwas further purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-093e4bf71b5c4991a2962cc5e9b6b383
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

Loading…