Acetic Acid → HCID 10224407, compound

HRID 1745903Notes

Reaction equation

HRID 1745903 reaction equation
[CH2:1]([O:3][C:4]1[CH:29]=[CH:28][C:7]2[N:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[C:14]([N:21]5[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]5)[CH:15]=[CH:16][CH:17]=4)[N:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1)[CH3:2].[CH:30]1([NH2:33])[CH2:32][CH2:31]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:30]1([NH:33][CH:24]2[CH2:23][CH2:22][N:21]([C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:13]=3[N:12]=[C:11]([N:8]3[C:7]5[CH:28]=[CH:29][C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]=5[N:10]=[CH:9]3)[CH:20]=[CH:19]4)[CH2:26][CH2:25]2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 10110689HCID 10110689, compound

Product 1

HCID 10224407HCID 10224407, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-[2-(5-Ethoxy-benzoimidazol-1-yl)quinolin-8-yl]-piperidin-4-one 18 (130 mg, 0.340 mMol) was dissolved in 1.5 mL of DCE under an atmosphere of dry N2. To this solution was added cyclopropyl amine (110 μL, 1.70 mMol) and 200 μL of AcOH and the solution was stirred for 10 minutes. To this solution was added NaHB(OAc)3 (107 mg, 0.50 mMol) and the solution was stirred at ambient temperature for 5 hours. The reaction mixture was then partitioned between DCM and aqueous 0.1 N NaOH. The DCM layer was again washed with aqueous 0.1 N NaOH, dried over Na2SO4, filtered and concentrated under vacuum to give 150 mg of a green foam. The foam was chromatographed on flash silica gel eluting with a gradient from MeOH/DCM (299) to MeOH/DCM (496) to give the title compound 20 as a yellow solid.

Workup

  1. stirringthe solution was stirred at ambient temperature for 5 hours
  2. customThe reaction mixture was then partitioned between DCM and aqueous 0.1 N NaOH
  3. washThe DCM layer was again washed with aqueous 0.1 N NaOH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4345f3976fb14c11bc993238d728fe38
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

Loading…