Acetone → HCID 11722404, compound

HRID 1784962Notes

Reaction equation

HRID 1784962 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)=[O:12])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]([CH3:23])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C(O)(=O)C>[CH:21]([NH:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]([N:13]3[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]3)=[O:12])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)([CH3:23])[CH3:20]

Participants

6

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 10244311HCID 10244311, compound

Product 1

HCID 11722404HCID 11722404, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (4-amino-1H-benzoimidazol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 43; 50 mg, 0.19 mmol) in dichloroethane (10 mL), was added acetone (0.07 mL, 0.96 mmol) and acetic acid (10 drops), followed by NaBH(OAc)3 (203 mg, 0.96 mmol). The reaction mixture was stirred at room temperature for 16 h, and then was quenched with satd aq NaHCO3 (5 mL). The aqueous layer was extracted with CHCl3 (10 mL), and the combined organic layers were dried (Na2SO4) and then concentrated under reduced pressure. The crude product was purified on silica gel (10 g; 0-10% methanol (2 M NH3)/CH2Cl2) to give 35 mg of the title compound (60%). MS (ESI): mass calculated for C16H23N5O, 301.39; m/z found, 302.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 11.11-11.07 (s, 1H), 7.18 (t, J=7.8 Hz, 1H), 6.76 (d, J=7.8 Hz, 1H), 6.37 (d, J=7.8 Hz, 1H), 4.80-4.65 (m, 2H), 3.92-3.78 (m, 2H), 2.56-2.53 (m, 4H), 2.36 (s, 3H), 1.85-1.81, (m, 1H), 1.32 (d, J=6.3 Hz, 6H).

Workup

  1. customwas quenched with satd aq NaHCO3 (5 mL)
  2. extractionThe aqueous layer was extracted with CHCl3 (10 mL)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified on silica gel (10 g; 0-10% methanol (2 M NH3)/CH2Cl2)

Sources & evidence

ORD record
ord-6b25c3dfbe1947958b939819f085e635
Source dataset
uspto-grants-2009_03
Patent number
US07504426B2

Reaction notes

Loading…