Acetic Acid → HCID 68288342, compound

HRID 541462Notes

Reaction equation

HRID 541462 reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:7][NH:6][CH2:5][C:4]2[NH:8][C:9]([C:11]3[C:12]([CH3:34])=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=4)[CH2:20][CH2:19]3)=[O:17])=[N:10][C:3]1=2.C(O)(=O)C.[Na].[CH3:41][C:42]([CH3:44])=O>CN(C=O)C>[CH:42]([N:6]1[CH2:7][C:2]([CH3:35])([CH3:1])[C:3]2[N:10]=[C:9]([C:11]3[C:12]([CH3:34])=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([N:18]3[CH2:19][CH2:20][CH:21]([C:24]4[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=4)[CH2:22][CH2:23]3)=[O:17])[NH:8][C:4]=2[CH2:5]1)([CH3:44])[CH3:41]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5360545SodiumHCID 68352705HCID 68352705, compound

Product 1

HCID 68288342HCID 68288342, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1-(5-(7,7-Dimethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile (0.12 g, 0.26 mmol) (intermediate prepared in the synthesis of compound 451), DMF (4 mL), acetic acid (69 μL, 1.21 mmol), sodium triacetoxyborohydide (0.11 g, 0.52 mmol) and acetone (0.50 mL, 6.8 mmol) were mixed and stirred at room temperature for 2 hours. The reaction was carefully quenched with water (10 mL) and the mixture was extracted with ethyl acetate (60 mL) and the organics was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by preparative TLC (DCM/10% MeOH) followed by a second preparative TLC (ethyl acetate/5% MeOH) to obtain the title compound as a white powder (4.1 mg, 8.1%). m/z (ES+) 510 (M+H)+.

Workup

  1. additionwere mixed
  2. customThe reaction was carefully quenched with water (10 mL)
  3. extractionthe mixture was extracted with ethyl acetate (60 mL)
  4. dry with materialthe organics was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by preparative TLC (DCM/10% MeOH)

Sources & evidence

ORD record
ord-7720758174c24b4e8b59e6ce3753bcca
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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