Sulfuric Acid → HCID 67775937, compound

HRID 1037567Notes

Reaction equation

HRID 1037567 reaction equation
[CH:1]1([C:4]2[C:12]([CH:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH:15]=[O:16])=[CH:11][C:10]3[C:6](=[C:7]([C:28]([NH:30][CH3:31])=[O:29])[N:8]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.C1(C2C(C(S(C)(=O)=O)CC(O)O)=CC3C(=C(C(NC)=O)N(C4C=CC(C)=CC=4)N=3)C=2)CC1.[BH4-].[Na+].S(=O)(=O)(O)O>O1CCOCC1.O>[CH:1]1([C:4]2[C:12]([CH:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH2:15][OH:16])=[CH:11][C:10]3[C:6](=[C:7]([C:28]([NH:30][CH3:31])=[O:29])[N:8]([C:21]4[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 67774005HCID 67774005, compoundHCID 88415470HCID 88415470, compound

Product 1

HCID 67775937HCID 67775937, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of an approximately 1:1 mixture of compound (v) and compound (vi) (14.2 mg, 0.032 mmol) in 1,4-dioxane (5 mL) and water (5 mL) was added sodium borohydride (28 mg, 0.74 mmol) and the reaction was stirred at RT for 1 h. The reaction mixture was acidified with 2 N aqueous sulfuric acid, then diluted with water (15 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (7 mL), dried (MgSO4) and evaporated to dryness. The residue was purified by flash column chromatography eluting with EtOAc/heptane (50-100%) to give racemic 5-cyclopropyl-6-[3-hydroxy-1-(methylsulfonyl)propyl]-N-methyl-2-(4-methylphenyl)-2H-indazole-3-carboxamide (viii) as a white solid (11 mg, 79%).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic extracts were washed with brine (7 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was purified by flash column chromatography
  6. washeluting with EtOAc/heptane (50-100%)

Sources & evidence

ORD record
ord-a0634f7b892e4132943e44ddee380ec4
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

Loading…