Acetonitrile → HCID 53680224, compound

HRID 362595Notes

Reaction equation

HRID 362595 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:16])=[C:10](F)[C:11]=2[O:13][CH3:14])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2].[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.COB(OC)OC.C(#N)C>O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:16])=[C:10]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:11]=2[O:13][CH3:14])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8082PiperidineHCID 8470Trimethyl borateHCID 14071840HCID 14071840, compound

Product 1

HCID 53680224HCID 53680224, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.83 g of 1-ethyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (10 mmol), 1.70 g of piperidine (20 mmol), 1.04 g of trimethoxyborane (10 mmol) and 15 ml of acetonitrile was refluxed with heating for 4.5 hours. The reaction solution was cooled to room temperature, 30 ml of water was added therein, a pH was adjusted to 8 with 6N--HCl, and separated crystals were filtered and dried to obtain 2.20 g of the objective compound.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 4.5 hours
  3. customHCl, and separated crystals
  4. filtrationwere filtered
  5. customdried

Sources & evidence

ORD record
ord-6b4205524e5949cbb3162b5f16710a3f
Source dataset
uspto-grants-1999_02
Patent number
US05869661

Reaction notes

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