Formaldehyde → HCID 11191429, compound

HRID 352964Notes

Reaction equation

HRID 352964 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=O.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C.C(N(CC)CC)C>[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]([CH3:35])[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

8

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11397823HCID 11397823, compound

Product 1

HCID 11191429HCID 11191429, compoundYield 129.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

In methylene chloride (4.5 ml), 2-[[4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazin-1-yl]carbonyl]-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine hydrochloride (200 mg) was suspended, followed by the addition of triethylamine (125 μl), acetic acid (77.0 μl), formaldehyde (a 37% aqueous solution, 56.1 μl) and sodium triacetoxyborohydride (139 mg) at room temperature. The resulting mixture was stirred for 15 minutes. To the reaction mixture, a saturated aqueous solution (20 ml) of sodium bicarbonate and methylene chloride (10 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 (25 g of silica gel, methylene chloride:methanol 10:1→7:1). The resulting solid was dissolved in a 1N aqueous hydrochloride in ethanol. After concentration of the resulting solution, water was added to the concentrate and the mixture was concentrated again, whereby the title compound (133 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 (25 g of silica gel, methylene chloride:methanol 10:1→7:1)
  7. dissolutionThe resulting solid was dissolved in a 1N aqueous hydrochloride in ethanol
  8. additionAfter concentration of the resulting solution, water was added to the
  9. concentrationconcentrate
  10. concentrationthe mixture was concentrated again

Sources & evidence

ORD record
ord-f9bfd5662f5b4cf6a003bf89be4fde80
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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