Thionyl Chloride → 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbonyl chloride

HRID 426995Notes

Reaction equation

HRID 426995 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][CH:4]=[C:3]1[C:12]([OH:14])=O.S(Cl)([Cl:17])=O.C[Si](C([Si](C)(C)C)C(N)=O)(C)C>C(Cl)Cl>[O:1]=[C:2]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][CH:4]=[C:3]1[C:12]([Cl:17])=[O:14]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 2915304-Oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acidHCID 11708267Bistrimethylsilylacetamid

Product 1

HCID 205444734-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to that of Example 1--1), 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbonyl chloride, which was prepared from 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (1.8 g) and thionyl chloride (36 ml), was treated with a solution of 7-(D-2-phenylglycinamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid formate (2.5 g) and bis(trimethylsilyl)acetamide (4.0 g) in methylene chloride (50 ml). Thus obtained reaction mixture was worked up in a similar manner to that of Example 1-4) to give powder (650 mg) of 7-[D-2-(4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxamido)-2-phenylacetamide]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid, mp 103° to 105° C. (dec).

Workup

  1. customThus obtained reaction mixture

Sources & evidence

ORD record
ord-5e5aaf4ab7184c74ad64c3b817474fa8
Source dataset
uspto-grants-1979_10
Patent number
US04172198

Reaction notes

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