Triethylamine → HCID 22710460, compound

HRID 352943Notes

Reaction equation

HRID 352943 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.C(N(CC)CC)C.ClC([O:43][CH2:44][CH3:45])=O.[BH4-].[Na+]>O1CCCC1.O>[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]([CH2:45][CH2:44][OH:43])[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 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 11272253HCID 11272253, compound

Product 1

HCID 22710460HCID 22710460, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude product, which had been obtained by the reaction in the same manner as in Example B-32 by using 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine hydrochloride (132 mg) and glyoxylic hydrate (82 mg) as starting materials, was suspended in tetrahydrofuran (50 ml). Triethylamine (0.22 ml) and ethyl chloroformate (0.03 ml) were added to the resulting suspension under ice cooling, followed by stirring at room temperature for 15 minutes. To the reaction mixture, sodium borohydride (50 mg) and water (10 ml) were added to the reaction mixture and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with dichloromethane, washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol 100:3), followed by dissolution in saturated hydrochloride in ethanol (1 ml). The resulting solution was then concentrated under reduced pressure. The concentrate was pulverized and washed in ethyl acetate, whereby the title compound (52 mg, 33%) was obtained.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. distillationby distilling off the solvent under reduced pressure
  8. customwas purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol 100:3)
  9. dissolutionfollowed by dissolution in saturated hydrochloride in ethanol (1 ml)
  10. concentrationThe resulting solution was then concentrated under reduced pressure
  11. washwashed in ethyl acetate

Sources & evidence

ORD record
ord-00dadb7fcd9240779ac8375030d77f5a
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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