Hydrochloric Acid → (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoroacrylic acid

HRID 2376136Notes

Reaction equation

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

Participants

Conditions

Temperature: 77.5 °C

Procedure

A mixture of ethyl (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoroacrylate (710 mg) and 1N NaOH solution (3.8 ml) in MeOH (20 ml) was stirred at 75-80° C. for 2 hours. To the reaction mixture was added 1N HCl solution (3.8 ml) and the resultant solution was evaporated in vacuo and the residue was dissolved in a mixture of MeOH and toluene and evaporated in vacuo and the residue was dried to give (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoroacrylic acid (658 mg).

Workup

customthe resultant solution was evaporated in vacuo
dissolutionthe residue was dissolved in a mixture of MeOH and toluene
customevaporated in vacuo
customthe residue was dried

Sources & evidence

ORD record: ord-be9b956f3b304934862a97e87d805610
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465731B2

Reaction notes

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