Ethyl 2-butyryl-3-ethoxyacrylate → HCID 178450498, compound

HRID 618449Notes

Reaction equation

HRID 618449 reaction equation
[NH2:1][C:2]1[C:3]([O:8][CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:11]([C:16](=[CH:22]OCC)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:15])[CH2:12][CH2:13][CH3:14]>>[C:11]([C:16](=[CH:22][NH:1][C:2]1[C:3]([O:8][CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:15])[CH2:12][CH2:13][CH3:14].[C:11]([C:16]1[C:17](=[O:18])[C:7]2[C:2](=[C:3]([O:8][CH2:9][CH3:10])[N:4]=[CH:5][CH:6]=2)[NH:1][CH:22]=1)(=[O:15])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 3359484Ethyl 2-butyryl-3-ethoxyacrylateHCID 167915952-Ethoxypyridin-3-amine

Product 2

HCID 21850851HCID 21850851, compoundYield 86%HCID 178450498HCID 178450498, compoundYield 93%

Procedure

Ethyl 2-butyryl-3-(2-ethoxypyridin-3-yl)aminoacrylate (93%) was prepared from 3-amino-2-ethoxypyridine and ethyl 2-butyryl-3-ethoxyacrylate by following the procedure similar to that of Example 18(A), and then the product was subjected to cyclization in a similar manner to that of Example 18(B) to give 3-butyryl-8-ethoxy-1,7-naphthyridin-4(1H)-one (86%), which is then subjected to methanesulfonylation in a similar manner to that of Example 18(C) to give 3-butyryl-8-ethoxy-4-methanesulfonyloxy-1,7-naphthyridine (67%).

Sources & evidence

ORD record
ord-489de82b104d4e12a6a71622f3659307
Source dataset
uspto-grants-1999_09
Patent number
US05952504

Reaction notes

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