HCID 23138620, compound → HCID 23139182, compound

HRID 1171663Notes

Reaction equation

HRID 1171663 reaction equation
[ClH:1].[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[N:26]([CH2:27][C:28]([O:30]CC)=[O:29])[N:25]=[CH:24][CH: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>Cl>[ClH:1].[C:28]([CH2:27][N:26]1[C:22](/[CH:21]=[C:16]2\[CH2:15][N:14]([CH:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[F:13])[C:5]([CH:2]3[CH2:3][CH2:4]3)=[O:33])[CH2:19][CH2:18][CH:17]\2[SH:20])=[CH:23][CH:24]=[N:25]1)([OH:30])=[O:29]

Participants

3

Reactant 1

HCID 23138620HCID 23138620, compound

Product 1

HCID 23139182HCID 23139182, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-{[1-(ethoxycarbonylmethyl)-1H-pyrazol-5-yl]methylidene}-4-sulfanylpiperidine hydrochloride (70 mg) in 3N aqueous hydrochloric acid solution (15 ml), and the resulting mixture was stirred at 50° C. for 2.5 hours. The reaction mixture was concentrated in vacuo, and the residue was purified by a preparative HPLC [YMC-Pack ODS-A; YMC, mobile phase: 25 to 27% acetonitrile/water (0.02% aqueous hydrochloric acid solution)] to afford the title compound (50 mg, yield: 75%) as a pale yellow amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by a preparative HPLC [YMC-Pack ODS-A; YMC, mobile phase: 25 to 27% acetonitrile/water (0.02% aqueous hydrochloric acid solution)]

Sources & evidence

ORD record
ord-9812cbfe2bc84a38b7d7dc90b8cc633b
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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