Pyridine → HCID 86609462, compound

HRID 1171719Notes

Reaction equation

HRID 1171719 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][C@H:18]\2[SH:19])=[N:8]1)([OH:4])=[O:3].N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>ClCCl>[ClH:1].[C:39]([S:19][C@@H: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:41])[CH3:40]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86609464HCID 86609464, compound

Product 1

HCID 86609462HCID 86609462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4R)-(E)-3-{[1-(2-carboxyethyl)-1H-pyrazol-3-yl]methylidene}-1-[(1RS)-2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidine hydrochloride (249.4 mg) in dichloromethane (12 ml) were added pyridine (0.24 ml) and acetic anhydride (0.24 ml) at 0° C. After the mixture was stirred at room temperature for 2.5 hours, solvents were removed under reduced pressure and the residue was purified by silica gel chromatography using dichloromethane and methanol (99:1 to 93:7) as eluents to afford the free base of the title compound (75.5 mg), which was treated in acetonitrile (2 ml) with a 4N hydrogen chloride dioxane solution (120 μl). The solvent and excess hydrogen chloride were removed under reduced pressure to afford the title compound (79.4 mg, yield: 29%) as a pale yellow amorphous solid.

Workup

  1. customsolvents were removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-54c35a6eeae54b0a8bed3767cfc0dead
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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