Hydrochloric Acid → HCID 23138682, compound

HRID 1171727Notes

Reaction equation

HRID 1171727 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:23]([CH2:27][C:28]([O:30]CC)=[O:29])[CH:24]=[CH:25][N:26]=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:23]1[CH:24]=[CH:25][N:26]=[C:22]1/[CH:21]=[C:16]1\[CH2:15][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[CH2:3][CH2:4]2)=[O:33])[CH2:19][CH2:18][CH:17]\1[SH:20])([OH:30])=[O:29]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23138827HCID 23138827, compound

Product 1

HCID 23138682HCID 23138682, compoundYield 101.5%

Procedure

Following a procedure similar to that described in Example 134, (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-2-yl]methylidene}-4-sulfanylpiperidine hydrochloride (155.6 mg) was treated with 3N hydrochloric acid (5 ml) at 50° C. for 2.5 hours. After the reaction solution of was concentrated under reduced pressure, the residue was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.024 N hydrochloric acid, 15/85, v/v) to afford the title compound (149.0 mg, yield: quantitative) as a colourless amorphous solid.

Workup

  1. concentrationAfter the reaction solution of was concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.024 N hydrochloric acid, 15/85, v/v)

Sources & evidence

ORD record
ord-31585d4717584ae9b920baf79a5a754a
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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