Methanol → N-Methyl-4-[4-[2-(1-methyl-2-oxo-3,4-dihydroquinolin-5-yl)ethyl]piperazin-1-yl]benzofuran-2-carboxamide

HRID 1471668Notes

Reaction equation

HRID 1471668 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[C:7]([CH2:12][CH:13]=O)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:15].[CH3:16][NH:17][C:18]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[C:23]=2[CH:24]=1)=[O:19].CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[CH3:16][NH:17][C:18]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[CH2:34][CH2:33][N:32]([CH2:13][CH2:12][C:7]4[CH:8]=[CH:9][CH:10]=[C:11]5[C:6]=4[CH2:5][CH2:4][C:3](=[O:15])[N:2]5[CH3:1])[CH2:31][CH2:30]3)[C:23]=2[CH:24]=1)=[O:19]

Participants

7

Reactant 4

HCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 574059892-(1-Methyl-2-oxo-3,4-dihydroquinolin-5-yl)acetaldehydeHCID 57405990N-methyl-4-piperazin-1-yl-benzofuran-2-carboxamide

Product 1

HCID 57388132N-Methyl-4-[4-[2-(1-methyl-2-oxo-3,4-dihydroquinolin-5-yl)ethyl]piperazin-1-yl]benzofuran-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-(1-Methyl-2-oxo-3,4-dihydroquinolin-5-yl)acetaldehyde (Example 1j, 0.50 g, 2.5 mmol) dissolved in dichloromethane (12 mL) was added to neat N-methyl-4-piperazin-1-yl-benzofuran-2-carboxamide (Example 1e, 0.542 g, 2.09 mmol). Methanol (2 mL) was added and the mixture was stirred at ambient temp for 20 min. Sodium triacetoxyborohydride (0.782 g, 3.69 mmol) was added and the mixture was stirred over the weekend. The mixture was diluted with dichloromethane and water. The organic phase was separated, dried over MgSO4, filtered, concentrated and purified by ISCO (0 to 8% 7 N ammonia/methanol in dichloromethane) to give of the title compound as a solid. Yield: 0.77 g, 70% 1H NMR (500 MHz, CDCl3) δ ppm 2.58-2.71 (m, 4H) 2.78 (br. s., 4H) 2.87-3.00 (m, 4H) 3.06 (d, 3H) 3.31 (br. s., 4H) 3.38 (s, 3H) 6.63 (d, 1H) 6.72 (d, 1H) 6.91 (d, 1H) 6.98 (d, 1H) 7.10 (d, 1H) 7.23 (t, 1H) 7.32 (t, 1H) 7.53 (s, 1H). MS m/z 447.2 [M+H]+.

Workup

  1. stirringthe mixture was stirred over the weekend
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by ISCO (0 to 8% 7 N ammonia/methanol in dichloromethane)

Sources & evidence

ORD record
ord-42c01652dac14ebab6a907a4fb7487e9
Source dataset
uspto-grants-2015_04
Patent number
US09012457B2

Reaction notes

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