3-Acetamidopyrrolidine → Ethyl 3-[6-(3-acetylamino-1-pyrrolidinyl)-2-chloro-5-fluoropyridin-3-yl]-3-oxopropionate
Reaction equation
[Cl:1][C:2]1[C:7]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:5]([F:16])=[C:4](Cl)[N:3]=1.[C:18]([NH:21][CH:22]1[CH2:26][CH2:25][NH:24][CH2:23]1)(=[O:20])[CH3:19]>>[C:18]([NH:21][CH:22]1[CH2:26][CH2:25][N:24]([C:4]2[N:3]=[C:2]([Cl:1])[C:7]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:5]=2[F:16])[CH2:23]1)(=[O:20])[CH3:19]Participants
3
Procedure
Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxo-propionate (1.4 g) prepared in Reference Example 10-(3) was allowed to react with 3-acetylaminopyrrolidine to give ethyl 3-[6-(3-acetylamino-1-pyrrolidinyl)-2-chloro-5-fluoropyridin-3-yl]-3-oxopropionate (0.78 g) as a oil. This compound (0.74 g) was treated with ethyl orthoformate and acetic anhydride, and the resulting oil, ethyl 2-[6-(3-acetylamino-1-pyrrolidinyl)-2-chloro-5-fluoronicotinoyl]-3-ethoxyacrylate, was allowed to react with cyclopropylamine to give ethyl 2-[6-(3-acetylamino-1-pyrrolidinyl)-2-chloro-5-fluoronicotinoyl]-3-cyclopropylaminoacrylate (0.43 g) as an amorphous powder, m.p. 71°-75° C.
Sources & evidence
- ORD record
- ord-4081244cb6c84c928c1bbbc78e86fb47
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04649144
Reaction notes
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