Hydrochloric Acid → HCID 86609481, compound

HRID 1171746Notes

Reaction equation

HRID 1171746 reaction equation
[C:1]([S:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH2:7]/[C:6]/1=[CH:24]\[C:25]1[N:26]=[N:27][N:28]([CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:44])[NH:35][O:36][Si](C(C)(C)C)(C)C)[CH:29]=1)(=[O:3])[CH3:2].[ClH:45]>ClCCl.O1CCOCC1>[ClH:45].[C:1]([S:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH2:7]/[C:6]/1=[CH:24]\[C:25]1[N:26]=[N:27][N:28]([CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:44])[NH:35][OH:36])[CH:29]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86609483HCID 86609483, compound

Product 1

HCID 86609481HCID 86609481, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-3-[(1-{4-[N-(t-butyldimethylsilyloxy)carbamoyl]butyl}-1H-1,2,3-triazol-4-yl)methylidene]-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidine (148 mg) in dichloromethane (3 ml) was added 4N solution of hydrogen chloride in dioxane (230 μl) at 0° C. The resulting mixture was stirred at room temperature for 15 minutes. The solvent and excess hydrogen chloride were removed in vacuo, and the residue was purified by chromatography on silica gel using a mixture of methanol and dichloromethane (3:97 to 15:85) as the eluent to afford (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-({1-[4-(N-hydroxycarbamoyl)butyl]-1H-1,2,3-triazol-4-yl}methylidene)piperidine hydrochloride (110 mg).

Workup

  1. customThe solvent and excess hydrogen chloride were removed in vacuo
  2. customthe residue was purified by chromatography on silica gel using
  3. additiona mixture of methanol and dichloromethane (3:97 to 15:85) as the eluent

Sources & evidence

ORD record
ord-49f38033bf5a47a7b4c9b17766a8660d
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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