Hydrochloric Acid → HCID 67128803, compound

HRID 2354086Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]3[N:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[C:24]([O:26]C)=[O:25])=[N:20][CH:21]=3)[CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]3[N:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])=[N:20][CH:21]=3)[CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of methyl (2E)-3-[5-({(3R)-1-[2-(3-fluorophenyl)ethyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylate (235 mg) and 1N—NaOH aq. (1.3 mL) in MeOH (4.7 mL) was heated at 50° C. for 3 hours. After cooling, 1N—HCl (1.37 mL) was added to the solution. The mixture was evaporated and azeotroped with dioxane and toluene to give a crude (2E)-3-[5-({(3R)-1-[2-(3-fluorophenyl)ethyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylic acid (226 mg).

Workup

temperatureAfter cooling
customThe mixture was evaporated
customazeotroped with dioxane and toluene

Sources & evidence

ORD record: ord-95084bed9deb440baf548900d661b497
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750155B2

Reaction notes

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