Aluminium lithium hydride → HCID 56646548, compound

HRID 1773604Notes

Reaction equation

HRID 1773604 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[CH:13]=[C:14]2[S:20][CH:19]=[C:18]([C:21](=[O:35])[NH:22][C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][C:32]=3[O:33][CH3:34])[N:29]=[CH:28][CH:27]=[CH:26]4)[C:15]2=[N:16][CH:17]=1)=O)C>O1CCCC1>[CH3:34][O:33][C:32]1[CH:31]=[C:30]2[C:25]([CH:26]=[CH:27][CH:28]=[N:29]2)=[CH:24][C:23]=1[NH:22][C:21]([C:18]1[C:15]2=[N:16][CH:17]=[C:12]([CH2:10][OH:9])[CH:13]=[C:14]2[S:20][CH:19]=1)=[O:35]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66664569HCID 66664569, compound

Product 1

HCID 56646548HCID 56646548, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminum hydride (3.5 M in toluene, 0.1 mL) was added to a suspension of 3-(7-methoxy-quinolin-6-ylcarbamoyl)-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (30 mg) in tetrahydrofuran (2 mL) and the resulting orange solution was stirred for 10 minutes. The reaction mixture was then quenched by addition of a saturated aqueous solution of ammonium chloride. The resulting mixture was filtered through a CELITE™ pad and the filter cake was washed with ethyl acetate. The filtrate was separated and the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM/MeOH, 97/3) to give 8 mg of 6-hydroxymethyl-thieno[3,2-b]pyridine-3-carboxylic acid (7-methoxy-quinolin-6-yl)-amide as an off-white solid. MS=365 [M+H]+.

Workup

  1. customThe reaction mixture was then quenched by addition of a saturated aqueous solution of ammonium chloride
  2. filtrationThe resulting mixture was filtered through a CELITE™ pad
  3. washthe filter cake was washed with ethyl acetate
  4. customThe filtrate was separated
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography (DCM/MeOH, 97/3)

Sources & evidence

ORD record
ord-b940af681a5043838cd28d34fd3a4d6a
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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