6-Chloronicotinamide → HCID 12862366, compound

HRID 904528Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH2:10])=[O:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[S:13][C:14]([CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:16]=1[C:17](OCC)=[O:18]>>[CH2:22]([C:14]1[S:13][C:12]2[N:11]=[C:2]3[CH:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[CH:6][N:7]3[C:17](=[O:18])[C:16]=2[CH:15]=1)[CH2:23][CH2:24][CH3:25]

Participants

Reactant 2

HCID 804566-Chloronicotinamide

HCID 12862357HCID 12862357, compound

Product 1

HCID 12862366HCID 12862366, compoundYield 15.8%

Procedure

From 6.2 g (0.040 mol) of 6-chloro-3-pyridinecarboxamide (Aldrich Chemical Company) and 9.0 g (0.040 mol) of 2-amino-5-butyl-3-thiophenecarboxylic acid, ethyl ester and heating in a wax bath at 180°-195° C. for one hundred forty-five minutes and then at 185°-200° C. for ninety minutes, following the procedure of Example 22 there is obtained 1.9 g of 2-butyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide; mp 266°-267° C. after recrystallization from glacial acetic acid.

Workup

waitat 185°-200° C. for ninety minutes

Sources & evidence

ORD record: ord-7bbdf1cf972b4c9193b341850ab5f71b
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04230707

Reaction notes

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