Acetic Anhydride → HCID 178471880, compound

HRID 1905926Notes

Reaction equation

C([O-])([O-])OCC.C(OC(=O)C)(=O)C.[C:14]([NH:17][CH:18]1[CH2:22][CH2:21][N:20]([C:23]2[C:40]([F:41])=[CH:39][C:26]([C:27]([C:29](=[CH:35]OCC)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:28])=[C:25]([Cl:42])[N:24]=2)[CH2:19]1)(=[O:16])[CH3:15].[CH:43]1([NH2:46])[CH2:45][CH2:44]1>>[C:14]([NH:17][CH:18]1[CH2:22][CH2:21][N:20]([C:23]2[C:40]([F:41])=[CH:39][C:26]([C:27]([C:29](=[CH:35][NH:46][CH:43]3[CH2:45][CH2:44]3)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:28])=[C:25]([Cl:42])[N:24]=2)[CH2:19]1)(=[O:16])[CH3:15]

Participants

Reactant 4

HCID 7918Acetic Anhydride

HCID 69828Cyclopropylamine

HCID 53630039Ethylorthoformate

HCID 73665910HCID 73665910, compound

Product 1

HCID 178471880HCID 178471880, compound

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-4029ba17832542ddb456e7033162c0b2
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04649144

Reaction notes

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