Hydrochloric Acid → ethyl (2Z)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}-2-fluoroacrylate dihydrochloride

HRID 226438Notes

Reaction equation

HRID 226438 reaction equation
[Cl:1][C:2]1[C:3]([NH:16][C@@H:17]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]2)=[N:4][CH:5]=[C:6](/[CH:8]=[C:9](\[F:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1.[ClH:29]>O1CCOCC1.CCO>[ClH:1].[ClH:29].[Cl:1][C:2]1[CH:7]=[C:6](/[CH:8]=[C:9](\[F:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[N:4][C:3]=1[NH:16][C@@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86603742tert-butyl (3R)-3-({3-chloro-5-[(1Z)-3-ethoxy-2-fluoro-3-oxo-1-propen-1-yl]-2-pyridinyl}amino)-1-pyrrolidinecarboxylate

Product 1

HCID 86603743ethyl (2Z)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}-2-fluoroacrylate dihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl (3R)-3-({3-chloro-5-[(1Z)-3-ethoxy-2-fluoro-3-oxo-1-propen-1-yl]-2-pyridinyl}amino)-1-pyrrolidinecarboxylate (2.34 g) and 4N hydrogen chloride in dioxane solution (11 ml) in EtOH (10 ml) was stirred at ambient temperature for 4 hours. IPE (100 ml) was added to a reaction mixture and the precipitate was collected by filtration to give ethyl (2Z)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}-2-fluoroacrylate dihydrochloride (1.95 g).

Workup

  1. additionIPE (100 ml) was added to a reaction mixture
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a7bfa96585b8493489315fd07549fdd4
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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