Sodium borohydride → HCID 18663199, compound

HRID 1956966Notes

Reaction equation

HRID 1956966 reaction equation
[CH3:1][C:2]1[C:3]([N:8]([CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:20][C:19]=3[CH:30]=[O:31])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7].[BH4-].[Na+]>CO>[CH3:1][C:2]1[C:3]([N:8]([CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:25]=[CH:26][CH:27]=[CH:28][N:29]=4)=[CH:20][C:19]=3[CH2:30][OH:31])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18663198HCID 18663198, compound

Product 1

HCID 18663199HCID 18663199, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-(4,5-dimethyl-3-isoxazolyl)-2'-formyl-N-[(2-methoxyethoxy)methyl]-4'-(2-pyrimidinyl)[1,1'-biphenyl]-2-sulfonamide (460 mg, 0.88 mmol, prepared as described in Step C of Example 16) in 10 ml MeOH, NaBH4 (40 mg, 1.06 mmol) was added. The reaction mixture was stirred at room temperature for 1.5 hrs and concentrated. To the residue, 10 ml H2O and 50 ml EtOAc were added. The organic layer was separated, washed with H2O, brine, dried and concentrated to give N-(4,5-dimethyl-3-isoxazolyl)-2'-(hydroxymethyl)-N-[(2-methoxyethoxy)methyl]-4'-(2-pyrimidinyl)[1,1'-biphenyl]-2-sulfonamide.

Workup

  1. concentrationconcentrated
  2. additionTo the residue, 10 ml H2O and 50 ml EtOAc were added
  3. customThe organic layer was separated
  4. washwashed with H2O, brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-118191cc8f614ac29fd26240081d6a7c
Source dataset
uspto-grants-1998_07
Patent number
US05780473

Reaction notes

Loading…