Formaldehyde → HCID 22709656, compound

HRID 352940Notes

Reaction equation

HRID 352940 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[S:25][C:26]4[CH2:27][NH:28][CH2:29][CH2:30][C:31]=4[N:32]=3)=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[CH2:33](N(CC)CC)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)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[CH2:17][CH2:18][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][CH:29]([CH3:33])[CH2:30][C:31]=4[N:32]=3)=[O:23])[CH2:20][CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 11272253HCID 11272253, compound

Product 1

HCID 22709656HCID 22709656, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (10 ml), 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine hydrochloride (400 mg) was suspended, followed by the addition of triethylamine (0.22 ml) and acetic acid (0.05 ml). The resulting mixture was stirred at room temperature for 5 minutes. To the reaction mixture, a 30% aqueous solution (0.08 ml) of formaldehyde and sodium triacetoxyborohydride (264 mg) were added. The resulting mixture was stirred at room temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue. The resulting mixture was washed with water and saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was dissolved in a saturated hydrochloride solution in ethanol (1 ml), followed by concentration under reduced pressure. The residue thus obtained was crystallized from hexane and ethyl acetate, whereby the title compound (298 mg, 71%) was obtained.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 10 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. washThe resulting mixture was washed with water and saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. dissolutionThe residue was dissolved in a saturated hydrochloride solution in ethanol (1 ml)
  9. concentrationfollowed by concentration under reduced pressure
  10. customThe residue thus obtained
  11. customwas crystallized from hexane and ethyl acetate, whereby the title compound (298 mg, 71%)
  12. customwas obtained

Sources & evidence

ORD record
ord-055ecedc7b7546dc9e7db62936175e47
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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