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

HRID 226397Notes

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-f57b190b038a4c4c84adc18698a2f268
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557127B2

Reaction notes

Loading…