Hydrochloric Acid → HCID 86609422, compound

HRID 1171664Notes

Reaction equation

HRID 1171664 reaction equation
[ClH:1].[C:2]([CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][C:9](/[CH:12]=[C:13]2\[CH2:14][N:15]([CH:20]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[C:21]([CH:23]3[CH2:25][CH2:24]3)=[O:22])[CH2:16][CH2:17][CH:18]\2[SH:19])=[N:8]1)([OH:4])=[O:3].[C:33](OC(=O)C)(=[O:35])[CH3:34].C(N(CC)CC)C.Cl>ClCCl.O1CCOCC1.O>[ClH:1].[C:33]([S:19][CH:18]1[CH2:17][CH2:16][N:15]([CH:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[C:21]([CH:23]2[CH2:25][CH2:24]2)=[O:22])[CH2:14]/[C:13]/1=[CH:12]\[C:9]1[CH:10]=[CH:11][N:7]([CH2:6][CH2:5][C:2]([OH:4])=[O:3])[N:8]=1)(=[O:35])[CH3:34]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23138580HCID 23138580, compound

Product 1

HCID 86609422HCID 86609422, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (E)-3-{[1-(2-carboxyethyl)-1H-pyrazol-3-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidine hydrochloride (90 mg) in dichloromethane (4 ml) were added acetic anhydride (0.09 ml) and triethylamine (0.13 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 3.5 hours. Subsequently, water (0.40 ml) was added to the reaction mixture. The resulting mixture was concentrated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of methanol and dichloromethane (3:200) as the eluent. To a solution of a colourless amorphous solid obtained in acetonitrile (3 ml) was added a 4N solution of hydrogen chloride in dioxane (0.07 ml) with stirring. The reaction mixture was concentrated in vacuo to afford the title compound (45 mg, yield: 43%) as a colourless amorphous solid.

Workup

  1. temperaturecooling
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. customthe residue was purified by chromatography on a silica gel column
  4. customTo a solution of a colourless amorphous solid obtained in acetonitrile (3 ml)
  5. stirringwith stirring
  6. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e2f6586ea3bb454e894195ba3fc64507
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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