Ethyl Acetate → ethyl (2E)-3-(2-{[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]amino}thiazol-4-yl)acrylate hydrochloride

HRID 226382Notes

Reaction equation

HRID 226382 reaction equation
[Cl:1][CH2:2][C:3](=O)/[CH:4]=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH:12]1([CH2:18][N:19]2[CH2:23][CH2:22][C@@H:21]([NH:24][C:25]([NH2:27])=[S:26])[CH2:20]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CCOC(C)=O>CC#N>[ClH:1].[CH:12]1([CH2:18][N:19]2[CH2:23][CH2:22][C@@H:21]([NH:24][C:25]3[S:26][CH:2]=[C:3](/[CH:4]=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:27]=3)[CH2:20]2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 86603623ethyl (2E)-5-chloro-4-oxo-2-pentenoateHCID 866036911-[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]thiourea

Product 1

HCID 86603689ethyl (2E)-3-(2-{[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]amino}thiazol-4-yl)acrylate hydrochlorideYield 60.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of ethyl (2E)-5-chloro-4-oxo-2-pentenoate (0.8 g) and 1-[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]thiourea (1.09 g) in CH3CN (16 mL) was stirred at 70° C. for 2 hrs. To the reaction mixture was added an AcOEt (32 mL) and isolated precipitate was collected by filtration to give ethyl (2E)-3-(2-{[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]amino}thiazol-4-yl)acrylate hydrochloride (1.10 g).

Workup

  1. customisolated precipitate
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-83b57657a4ae4f03af0d89a94a34850a
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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