Hydrochloric Acid → Ethyl (2E)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridyl}acrylate dihydrochloride

HRID 226416Notes

Reaction equation

HRID 226416 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][C@@H:16]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)=[N:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1.[ClH:28]>O1CCOCC1.CCO>[ClH:1].[ClH:28].[Cl:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[N:4][C:3]=1[NH:15][C@@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86603724tert-butyl (3R)-3-({3-chloro-5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-2-pyridinyl}amino)-1-pyrrolidinecarboxylate

Product 1

HCID 86603632Ethyl (2E)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridyl}acrylate dihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl (3R)-3-({3-chloro-5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-2-pyridinyl}amino)-1-pyrrolidinecarboxylate (0.98 g) and 4N hydrogen chloride in dioxane solution (5 ml) in EtOH (10 ml) was stirred at ambient temperature for 4 hours. The reaction mixture was evaporated in vacuo and the residue was triturated with hexane was collected by filtration to give ethyl (2E)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}acrylate dihydrochloride (0.9 g).ethyl (2E)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}acrylate dihydrochloride

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was triturated with hexane
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-75efb99766e74c8aabdd5423757021f2
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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