HCID 10049155, compound → HCID 10071379, compound

HRID 1179332Notes

Reaction equation

HRID 1179332 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[NH:23][C:22]3=[O:30])[CH2:17][CH2:16]2)[CH2:11][CH2:10]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[NH:23][C:22]3=[O:30])[CH2:17][CH2:16]2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 10049155HCID 10049155, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10071379HCID 10071379, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 29.7 mg of 1-[1-[1-(3-Chloro-2-thenoyl)piperidin-4-yl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one and 7 mg of lithium aluminum hydride in 1 ml of THF was stirred at 0° C. for 2 h and then quenched with Na2SO4—10H2O. The mixture was stirred overnight and the insoluble material was removed by filtration. The filtrate was concentrated and purified with PTLC (CHCl3/MeOH/28% aqueous NH3=120/10/1) to give 11.0 mg of the target compound as a colorless solid.

Workup

  1. customquenched with Na2SO4—10H2O
  2. stirringThe mixture was stirred overnight
  3. customthe insoluble material was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. custompurified with PTLC (CHCl3/MeOH/28% aqueous NH3=120/10/1)

Sources & evidence

ORD record
ord-cbb7db3316f14b60932d01a62b0e338d
Source dataset
uspto-grants-2007_10
Patent number
US07279490B2

Reaction notes

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