Triethylamine → ethyl (2E)-3-(5-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

HRID 2376083Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1.[Cl:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([N:22]2[CH2:26][CH2:25][C@@H:24]([NH2:27])[CH2:23]2)=[O:21])=[CH:18][CH:17]=1.CCN(CC)CC>CN(C=O)C>[Cl:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([N:22]2[CH2:26][CH2:25][C@@H:24]([NH:27][C:2]3[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=3)[CH2:23]2)=[O:21])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (500 mg) in DMF (5 mL) was added (3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamine (951 mg) and Et3N (1.15 mL). After stirring for 3 hours at 120° C., the reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with H2O, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(5-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (601 mg).

Workup

customthe reaction mixture was partitioned between ethyl acetate and H2O
washThe organic layer was washed with H2O
dry with materialdried over MgSO4
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-e0eeefb523a141e0b10cb6fd924da15b
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465731B2

Reaction notes

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