Dimethylformamide → HCID 15167906, compound

HRID 1494740Notes

Reaction equation

HRID 1494740 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH2:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][NH:23]1.C1CCN2C(=NCCC2)CC1.CN(C=O)C>C(O)(=O)C.C(Cl)(Cl)Cl>[CH2:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][N:23]1[C:11]1[C:12]([F:14])=[C:13]2[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]2[CH:1]2[CH2:3][CH2:2]2)=[C:9]([NH2:17])[C:10]=1[F:16]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 422478IsoindolineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 15167906HCID 15167906, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 200 mg of 1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 87 mg of isoindoline, 200 mg of DBU, and 1.5 ml of anhydrous DMF was heated at 110°-115° C. for 20 minutes while stirring. After cooling, 30 ml of chloroform and 10 ml of 5% acetic acid were added to the resulting reaction mixture. The mixture was thoroughly stirred and the organic layer was separated. The water layer was extracted once more with 20 ml of chloroform. The extract, mixed with the organic layer, was dried over magnesium sulfate, and condensed. The residue was recrystallized from a mixed solvent of chloroform and methanol to obtain 144 mg of the target compound.

Workup

  1. temperaturewas heated at 110°-115° C. for 20 minutes
  2. temperatureAfter cooling
  3. stirringThe mixture was thoroughly stirred
  4. customthe organic layer was separated
  5. extractionThe water layer was extracted once more with 20 ml of chloroform
  6. additionThe extract, mixed with the organic layer
  7. dry with materialwas dried over magnesium sulfate, and condensed
  8. customThe residue was recrystallized from a mixed solvent of chloroform and methanol

Sources & evidence

ORD record
ord-9c13582fa76e4dcd97cba31873bf295d
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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