Hydrochloric Acid → HCID 23138536, compound

HRID 1171655Notes

Reaction equation

HRID 1171655 reaction equation
Cl.[CH:2]1([C:5](=[O:33])[CH:6]([N:14]2[CH2:19][CH2:18][CH:17]([SH:20])/[C:16](=[CH:21]/[C:22]3[CH:26]=[CH:25][N:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:23]=3)/[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])[CH2:4][CH2:3]1.[C:34]([Cl:37])(=[O:36])[CH3:35].C(N(CC)CC)C.Cl>ClCCl.O1CCOCC1>[ClH:37].[C:34]([S:20][CH:17]1[CH2:18][CH2:19][N:14]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])[C:5]([CH:2]2[CH2:4][CH2:3]2)=[O:33])[CH2:15]/[C:16]/1=[CH:21]\[C:22]1[CH:26]=[CH:25][N:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:23]=1)(=[O:36])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 23138741HCID 23138741, compound

Product 1

HCID 23138536HCID 23138536, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-{[1-(ethoxycarbonylmethyl)-1H-pyrazol-3-yl]methylidene}-4-sulfanylpiperidine hydrochloride (140 mg) in dichloromethane (5 ml) were added acetyl chloride (0.02 ml) and triethylamine (0.12 ml), and the resulting mixture was stirred at room temperature for 40 minutes. To the resulting reaction mixture were added acetyl chloride (0.02 ml) and triethylamine (0.4 ml), and the resulting mixture was stirred at room temperature for 80 minutes. The reaction mixture was concentrated in vacuo, and the residue was purified by chromatography on a silica gel column using methanol and dichloromethane (1:19) as the eluent. The yellow oily product obtained was dissolved in dichloromethane (3 ml) and a 4N solution of hydrogen chloride in dioxane (0.11 ml) was added to the resulting solution. After evaporation of the solvent of the reaction mixture under reduced pressure, the title compound (70 mg, yield: 46%) was afforded as a pale yellow amorphous solid.

Workup

  1. customTo the resulting reaction mixture
  2. stirringthe resulting mixture was stirred at room temperature for 80 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by chromatography on a silica gel column
  5. customThe yellow oily product obtained
  6. customAfter evaporation of the solvent of the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-00a0900b9c6f4f77b42b515011707051
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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