P,P-Diphenylphosphinic azide → 6-Aminoquinoline

HRID 2289890Notes

Reaction equation

HRID 2289890 reaction equation
ClC1C=CC(CNC([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2O)=[CH:17][C:16](C(O)=O)=[CH:15][C:14]=3F)=O)=CC=1.C1(P([N:41]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C(O)(C)(C)C>[NH2:41][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:19]2

Participants

4

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 178524524HCID 178524524, compound

Product 1

HCID 113736-Aminoquinoline

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Compounds of the present invention may also be prepared by following the procedures described in Chart T. In CHART T, 3-{[(4-Chlorobenzyl)amino]-carbonyl}-8-fluoro-4-hydroxy-6-quinolinecarboxylic acid of example t-1 is converted to the 6-tert-butyl carbamate t-2 by treatment with diphenylphosphoryl azide in tert-butanol with heating. The carbamate is removed with trifluoroacetic acid to afford the 6-aminoquinoline t-3. The amine is sulfonylated with 4-methoxyphenylsulfonyl chloride in pyridine to yield the 6-sulfonamide t-4.

Workup

  1. customCompounds of the present invention may also be prepared
  2. customThe carbamate is removed with trifluoroacetic acid

Sources & evidence

ORD record
ord-9b433e6ff97843e89306fae41d27a413
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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