Formaldehyde → HCID 22709656, compound

HRID 1061073Notes

Reaction equation

HRID 1061073 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 formaldehyde solution (0.08 ml) and sodium triacetoxyborohydride (264 mg) were added, followed by stirring at room temperature for 10 minutes. After the reaction mixture was concentrated under reduced pressure, the residue was added with ethyl acetate. The resulting mixture was washed with water and saturated saline and then dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure The residue was dissolved in a saturated ethanol hydrochloride solution (1 ml) and then the resulting solution was concentrated under reduced pressure. The residue was crystallized from hexane and ethyl acetate, whereby the title compound (298 mg, 71%) was obtained.

Workup

  1. stirringby stirring at room temperature for 10 minutes
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. additionthe residue was added with ethyl acetate
  4. washThe resulting mixture was washed with water and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure The residue
  7. dissolutionwas dissolved in a saturated ethanol hydrochloride solution (1 ml)
  8. concentrationthe resulting solution was concentrated under reduced pressure
  9. customThe residue was crystallized from hexane and ethyl acetate, whereby the title compound (298 mg, 71%)
  10. customwas obtained

Sources & evidence

ORD record
ord-1ec0c2e8e6804df7afc86815aaa9deab
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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