Hydrochloric Acid → HCID 86609477, compound

HRID 1171741Notes

Reaction equation

HRID 1171741 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[CH:29]=[CH:28][N:27]([CH2:30][CH2:31][NH:32]C(OC(C)(C)C)=O)[N:26]=1)(=[O:3])[CH3:2].[ClH:40]>>[ClH:40].[ClH:40].[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[CH:29]=[CH:28][N:27]([CH2:30][CH2:31][NH2:32])[N:26]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86609479HCID 86609479, compound

Product 1

HCID 86609477HCID 86609477, compound

Procedure

A solution of (E)-4-(acetylsulfanyl)-3-({1-[2-(t-butoxycarbonylamino)ethyl]-1H-pyrazol-3-yl}methylidene)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidine (479 mg) in 4 N hydrogen chloride (in dioxane, 8 ml) was stirred at room temperature for one hour. The solvent and hydrogen chloride were removed in vacuo, and the residue was purified by chromatography on silica gel using a mixture of in ethanol and dichloromethane (2:98 to 20:80) as eluents to afford (E)-4-(acetylsulfanyl)-3-{[1-(2-aminoethyl)-1H-pyrazol-3-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidine dihydrochloride as a pale brown amorphous solid (450 mg). A part of the above compound (104.2 mg) was dissolved in ethanol (4 ml), and hydrogen chloride gas was passed therethrough with stirring at 0° C., and the resulting mixture was stirred under tightly sealed condition at room temperature for 5 hours. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel using a mixture of ethanol and dichloromethane (5:95 to 25:75) as the eluent to afford the title compound as a colourless amorphous solid (86.3 mg, overall yield: 90%).

Workup

  1. customThe solvent and hydrogen chloride were removed in vacuo
  2. customthe residue was purified by chromatography on silica gel using
  3. additiona mixture of in ethanol and dichloromethane (2:98 to 20:80) as eluents

Sources & evidence

ORD record
ord-96476a6dc33d4a78a0c48104b5a82d8a
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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