Sodium cyanoborohydride → HCID 12004116, compound

HRID 2241988Notes

Reaction equation

HRID 2241988 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[F:19][C:20]([F:39])([F:38])[C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][C:25]=2[N:31]1[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]1.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N:13]3[CH2:14][CH2:15][N:16]([CH:34]4[CH2:35][CH2:36][N:31]([C:25]5[CH:26]=[CH:27][CH:28]=[C:29]6[C:24]=5[N:23]=[CH:22][C:21]([C:20]([F:39])([F:38])[F:19])=[CH:30]6)[CH2:32][CH2:33]4)[CH2:17][CH2:18]3)[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 184141776-Methoxy-8-(piperazin-1-YL)quinolineHCID 59204871HCID 59204871, compound

Product 1

HCID 12004116HCID 12004116, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-methoxy-8-piperazinoquinoline (Example A, Step 4; 0.0825 g) and 1-[3-(trifluoromethyl)quinolin-8-yl]piperidin-4-one (0.1 g) in methanol (5 mL) was treated with sodium cyanoborohydride (Step 4, 0.032 g). The resulting mixture was stirred at room temperature for 18 hours and then concentrated on a rotary evaporator. The residue was taken up in CH2C2, washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give the desired product, which was converted to its dihydrochloride salt in using 1N HCl/Et2O to yield 0.035 g as a yellow solid; MS (ES) m/z (relative intensity): 522 (M+H)+ (100).

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-af40e8f542e442719f266a303d29f5e7
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

Loading…