Triethylamine → HCID 70207944, compound

HRID 1378392Notes

Reaction equation

HRID 1378392 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[OH:22][CH2:23][C@H:24]1[C@H:28]([C:29]([F:32])([F:31])[F:30])[CH2:27][NH:26][CH2:25]1.C(N(CC)CC)C>CS(C)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:26]4[CH2:27][C@@H:28]([C:29]([F:31])([F:32])[F:30])[C@H:24]([CH2:23][OH:22])[CH2:25]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 70207387HCID 70207387, compound

Product 1

HCID 70207944HCID 70207944, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

In 6 ml of dimethylsulfoxide, is dissolved 283 mg (1 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. To the above solution, are added 411 mg (2 mmol) of trans-3-hydroxymethyl-4-trifluoromethylpyrrolidine hydrochloride and 0.42 ml (3 mmol) of triethylamine. The mixture is stirred at 50° C. for 18 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue. The resulting precipitate was obtained by filtration and washed successively with water, isopropanol and diethyl ether to give 412 mg of the objective substance as a slightly yellow powder (yield 95.4%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. customThe resulting precipitate was obtained by filtration
  4. washwashed successively with water, isopropanol and diethyl ether

Sources & evidence

ORD record
ord-f43c8a87b5f34869ab4f00226a0f6297
Source dataset
uspto-grants-1997_09
Patent number
US05668147

Reaction notes

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