Sodium Bicarbonate → HCID 68991018, compound

HRID 656970Notes

Reaction equation

HRID 656970 reaction equation
[ClH:1].Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[N:15]=[CH:14][C:13]2=[O:23])[CH2:6][CH2:5]1.[O:24]1[C:28]2=[CH:29][N:30]=[C:31]([CH:33]=O)[CH:32]=[C:27]2[CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO.C(Cl)(Cl)Cl.C(N(CC)CC)C>[ClH:1].[ClH:1].[O:24]1[C:28]2=[CH:29][N:30]=[C:31]([CH2:33][NH:3][CH:4]3[CH2:5][CH2:6][N:7]([CH2:10][CH2:11][N:12]4[C:21]5[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=5)[N:15]=[CH:14][C:13]4=[O:23])[CH2:8][CH2:9]3)[CH:32]=[C:27]2[CH2:26][CH2:25]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 574231162,3-Dihydrofuro[2,3-c]pyridine-5-carbaldehydeHCID 688175421-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride

Product 1

HCID 68991018HCID 68991018, compoundYield 121.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride (60 mg; 0.166 mmol) and 2,3-dihydrofuro[2,3-c]pyridine-5-carbaldehyde (30 mg, 0.20 mmol) in MeOH (3 ml), chloroform (3 ml) and triethylamine (0.06 ml) was heated under reflux with 3A molecular sieves overnight. It was cooled and sodium triacetoxyborohydride (0.11 g; 0.52 mmol) was added, and the mixture was stirred at rt overnight. Aqueous sodium bicarbonate solution was added to basify and the aqueous phase was extracted several times with 10% MeOH-DCM. The organic fractions were dried and evaporated. Chromatography on silica gel, eluting with 0-20% MeOH-DCM gave the free base of the title compound (50 mg, 71%).

Workup

  1. temperatureIt was cooled
  2. extractionthe aqueous phase was extracted several times with 10% MeOH-DCM
  3. customThe organic fractions were dried
  4. customevaporated
  5. washChromatography on silica gel, eluting with 0-20% MeOH-DCM

Sources & evidence

ORD record
ord-2e988a1cf247447ab030f16fcd78a85e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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