Sodium borohydride → HCID 54403072, compound

HRID 1708554Notes

Reaction equation

HRID 1708554 reaction equation
[CH3:1][C:2]1[N:3]([C:11]2[CH:39]=[CH:38][C:14]([C:15]([N:17]3[CH2:22][CH2:21][C:20](=[C:23]4[C:32]5[CH:31]=[CH:30][S:29][C:28]=5[C:27](=[O:33])[CH2:26][C:25]5[CH:34]=[CH:35][CH:36]=[CH:37][C:24]4=5)[CH2:19][CH2:18]3)=[O:16])=[CH:13][CH:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[BH4-].[Na+]>CO>[OH:33][CH:27]1[C:28]2[S:29][CH:30]=[CH:31][C:32]=2[C:23](=[C:20]2[CH2:21][CH2:22][N:17]([C:15](=[O:16])[C:14]3[CH:13]=[CH:12][C:11]([N:3]4[C:4]5[CH:9]=[CH:8][N:7]=[CH:6][C:5]=5[N:10]=[C:2]4[CH3:1])=[CH:39][CH:38]=3)[CH2:18][CH2:19]2)[C:24]2[CH:37]=[CH:36][CH:35]=[CH:34][C:25]=2[CH2:26]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18958945HCID 18958945, compound

Product 1

HCID 54403072HCID 54403072, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzoyl]-4-(10-oxo-9,10-dihydro -4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)piperidine (200 mg, 0.38 mmol) (Example 8) and sodium borohydride (200 mg) in methanol (20 ml) was stirred at room temperature for 4 hours and evaporated. The residue was partitioned between dichloromethane and water and the organic layer was washed with water, dried over magnesium sulphate and evaporated. The residue was triturated with hexane to give the title compound (70 mg, 35%) as a colourless foam which was characterised as a dihydrate. Found: C,67.9; H,5.4; N,9.6. C32H28N4O2S. 2 H2O requires C,67.5; H,5.6; N,9.9%.

Workup

  1. customevaporated
  2. customThe residue was partitioned between dichloromethane and water
  3. washthe organic layer was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-bc8d20a74b7746f5906b28d0057609fb
Source dataset
uspto-grants-1994_10
Patent number
US05358953

Reaction notes

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