HCID 18797470, compound → HCID 18797336, compound

HRID 1003574Notes

Reaction equation

HRID 1003574 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=O)[CH2:9][N:10]1[CH2:15][CH:14]=[C:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH2:12][CH2:11]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:25][C:21]1[CH:20]=[C:19]2[C:24]([C:16]([C:13]3[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][NH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:11][CH:12]=3)=[CH:17][NH:18]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 18797470HCID 18797470, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18797336HCID 18797336, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.83 gm (2.28 mMol) N-(2-pyridinyl)-2-(4-(6-chloro-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl)acetamide in 20 mL tetrahydrofuran was added dropwise to a slurry of 0.130 gm (3.41 mMol) lithium aluminum hydride in 10 mL tetrahydrofuran at 0° C. at such a rate as to maintain the reaction temperature >5° C. The reaction mixture was then allowed to warm to room temperature over 2 hours. The reaction mixture was then quenched by the sequential addition of water, 15% aqueous sodium hydroxide, and water with vigorous stirring. The resulting slurry was filtered through a bed of celite and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a chloroform gradient containing 5-8% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.31 gm (39%) of the desired compound.

Workup

  1. temperatureto maintain the reaction temperature >5° C
  2. customThe reaction mixture was then quenched by the sequential addition of water, 15% aqueous sodium hydroxide, and water with vigorous stirring
  3. filtrationThe resulting slurry was filtered through a bed of celite
  4. concentrationthe filtrate concentrated under reduced pressure
  5. washeluting with a chloroform gradient
  6. additioncontaining 5-8% methanol
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a10d2c99b8da49989f0d83d06dfdb37b
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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