Hydrochloric Acid → (2E)-3-[5-({(3R)-1-[2-(dimethylamino) benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylic acid

HRID 2354089Notes

Reaction equation

[CH3:1][N:2]([CH3:28])[C:3]1[CH:27]=[CH:26][CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12]2[N:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([O:22]C)=[O:21])=[N:16][CH:17]=2)[CH2:7]1.[OH-].[Na+].Cl>CO>[CH3:28][N:2]([CH3:1])[C:3]1[CH:27]=[CH:26][CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12]2[N:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[N:16][CH:17]=2)[CH2:7]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of methyl (2E)-3-[5-({(3R)-1-[2-(dimethylamino) benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylate (235 mg) in MeOH (1.9 mL) was added 1N NaOH aq. (1.2 mL), which was stirred at 55° C. for 1 hour. To the reaction mixture was added 1N—HCl aq. (1.2 mL), and evaporated in vacuo to give a crude (2E)-3-[5-({(3R)-1-[2-(dimethylamino)benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylic acid as, a brown solid (0.310 mg). This was used next reaction without purification.

Workup

customevaporated in vacuo

Sources & evidence

ORD record: ord-0cd47b884fa8490099b9663803b4e17e
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750155B2

Reaction notes

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