Phosgene → HCID 178481179, compound

HRID 381652

Reaction equation

HRID 381652 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.C(Cl)(Cl)=O.[Na+].[CH3:17][S:18]([CH2-])=[O:19].C(O[CH2:29][CH3:30])(OCC)OCC.N1CCCC[CH2:32]1>C(O)(=O)C>[CH3:32][N:11]1[C:4]2[CH:3]=[C:2]([F:1])[CH:10]=[CH:9][C:5]=2[C:6](=[O:8])[C:29]([S+:18]([O-:19])[CH3:17])=[CH:30]1

Participants

7

Reactant 5

HCID 6371PhosgeneHCID 8082PiperidineHCID 31214Ethyl orthoformateHCID 27249674-Fluoroanthranilic acidHCID 10154010Methane, sulfinylbis-, ion(1-), sodium

Product 1

HCID 178481179HCID 178481179, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

starting with 4-fluoroanthranilic acid comprising cyclization with phosgene to create an intermediate -A, followed by methylation to create an intermediate -B, then by reaction with dimsyl sodium to create an intermediate -C, then by reaction with triethyl orthoformate in the presence of piperdine and acetic acid to give flosequinan. The overall yield of the disclosed process is greater than about 16%.

Sources & evidence

ORD record
ord-9604846a8b2848ef94d287caf71cf1df
Source dataset
uspto-grants-2001_10
Patent number
US06307050B1

Linked notes

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