Trimethyl borate → HCID 14962313, compound

HRID 362596Notes

Reaction equation

HRID 362596 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.COB(OC)OC>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 31268PyrrolidineHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 14962313HCID 14962313, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.95 g of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (10 mmol), 1.42 g of pyrrolidine (20 mmol), 1.04 g of trimethoxyborane (10 mmol) and 20 ml of acetonitrile was refluxed with heating for 3.5 hours. The reaction solution was cooled to room temperature, acetonitrile was distilled under vacuum and 15 ml of ethanol was added into the resultant product. Separated crystals were filtered and dried to obtain 3.05 g of the objective compound (88.2%).

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 3.5 hours
  3. distillationacetonitrile was distilled under vacuum and 15 ml of ethanol
  4. additionwas added into the resultant product
  5. customSeparated crystals
  6. filtrationwere filtered
  7. customdried

Sources & evidence

ORD record
ord-bdf965de8ddf453994d70c529dd5b3d0
Source dataset
uspto-grants-1999_02
Patent number
US05869661

Reaction notes

Loading…