Hydrochloric Acid → Ethyl (2E)-3-(5-{[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

HRID 2376053Notes

Reaction equation

HRID 2376053 reaction equation
[CH2:1]([O:3][C:4](=[O:27])/[CH:5]=[CH:6]/[C:7]1[N:8]=[CH:9][C:10]([NH:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20](OC(C)(C)C)=O)[CH2:15]2)=[N:11][CH:12]=1)[CH3:2].Cl>O1CCOCC1.CO.C(OCC)(=O)C.O>[CH:18]1([CH2:17][N:16]2[CH2:20][CH2:19][C@@H:14]([NH:13][C:10]3[N:11]=[CH:12][C:7](/[CH:6]=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:27])=[N:8][CH:9]=3)[CH2:15]2)[CH2:12][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 86603674tert-butyl (3R)-3-({5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-piperidinecarboxylate

Product 1

HCID 86603673Ethyl (2E)-3-(5-{[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (3R)-3-({5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-piperidinecarboxylate (6.26 g) in a mixture of 1,4-dioxane (25 mL) and MeOH (5 mL) was added 4N hydrogen chloride solution in ethyl acetate (30 mL) in water bath.

Sources & evidence

ORD record
ord-9abbfc3130df469a98bd8aef637ab53a
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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