Acetic Acid → HCID 22711055, compound

HRID 352965Notes

Reaction equation

HRID 352965 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[NH:32][C:31]4[CH2:30][CH2:29][NH:28][CH2:27][C:26]=4[CH:25]=3)=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[C:33](O)(=O)[CH3:34].C(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C.CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[NH:32][C:31]4[CH2:30][CH2:29][N:28]([CH2:33][CH3:34])[CH2:27][C:26]=4[CH:25]=3)=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11397823HCID 11397823, compound

Product 1

HCID 22711055HCID 22711055, compoundYield 103.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

In methylene chloride (3.0 ml), 2-[[4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazin-1-yl]carbonyl]-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine hydrochloride (149 mg) was suspended, followed by the addition of methanol (0.6 ml), triethylamine (82.5 μl), acetic acid (51.0 μl, 891 μmol), acetaldehyde (19.5 μl) and sodium triacetoxyborohydride (74.0 mg) at room temperature. The resulting mixture was stirred for 15 minutes. To the reaction mixture, a saturated aqueous solution (30 ml) of sodium bicarbonate and methylene chloride (15 ml) were added to separate the water layer. The resulting water layer was extracted with methylene chloride (2×10 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column (30 g of silica gel, methylene chloride:methanol=10:1). The resulting white solid was dissolved in a 1N aqueous hydrochloride in ethanol (10 ml). After concentration of the resulting solution, water (30 ml) was added to the concentrate and the mixture was concentrated again, whereby the title compound (81.7 mg) was obtained as a white solid.

Workup

  1. customto separate the water layer
  2. extractionThe resulting water layer was extracted with methylene chloride (2×10 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by chromatography on a silica gel column (30 g of silica gel, methylene chloride:methanol=10:1)
  7. dissolutionThe resulting white solid was dissolved in a 1N aqueous hydrochloride in ethanol (10 ml)
  8. additionAfter concentration of the resulting solution, water (30 ml) was added to the
  9. concentrationconcentrate
  10. concentrationthe mixture was concentrated again

Sources & evidence

ORD record
ord-e9fe26f2d6744f5f9a95cee2a4978cc9
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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