Hydrochloric Acid → HCID 23447359, compound

HRID 1840548Notes

Reaction equation

HRID 1840548 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH2:26][O:27][C:28]4[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:29]=4[CH:30]=3)(=[O:24])=[O:23])[CH2:18][C:17]2=[O:36])([OH:14])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C.CO>[Cl:35][C:33]1[CH:32]=[CH:31][C:29]2[CH:30]=[C:25]([S:22]([N:19]3[CH2:20][CH2:21][N:16]([CH2:15][C:11]4([OH:14])[CH2:12][CH2:13][N:8]([C:11]5[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=5)[CH2:9][CH2:10]4)[C:17](=[O:36])[CH2:18]3)(=[O:23])=[O:24])[CH2:26][O:27][C:28]=2[CH:34]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23447491HCID 23447491, compound

Product 1

HCID 23447359HCID 23447359, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-[1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-ylmethyl]-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinone (150 mg) were added 4N hydrochloric acid in ethyl acetate (8 ml) and methanol (4 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated, and to the residue were added 4-chloropyridine hydrochloride (81 mg), triethylamine (81 mg) and ethanol (20 ml). The mixture was allowed to react in a sealed tube at 150° C. for 15 hours. The reaction solution was concentrated, and the residue was purified with silica gel column chromatography (dichloromethane: methanol containing 10% ammonia solution=10: 1) to give colorless solid of the title compound (63 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionto the residue were added 4-chloropyridine hydrochloride (81 mg), triethylamine (81 mg) and ethanol (20 ml)
  3. customto react in a sealed tube at 150° C. for 15 hours
  4. concentrationThe reaction solution was concentrated
  5. customthe residue was purified with silica gel column chromatography (dichloromethane: methanol containing 10% ammonia solution=10: 1)

Sources & evidence

ORD record
ord-83da9b5cfc3945d1b662a6a17106fba9
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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