Triethylamine → HCID 14774111, compound

HRID 2073853Notes

Reaction equation

HRID 2073853 reaction equation
C([C:3]1[N:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[C:5]2[C:10]([C:11](=[O:16])[C:12]=1[C:13]([OH:15])=[O:14])=[C:9]([CH3:17])[C:8]([F:18])=[C:7](F)[C:6]=2[F:20])C.C(OC([NH:36][CH:37]1[CH2:41][CH2:40][NH:39][CH2:38]1)=O)(C)(C)C.C(N(CC)CC)C>C(#N)C>[NH2:36][CH:37]1[CH2:41][CH2:40][N:39]([C:7]2[C:6]([F:20])=[C:5]3[C:10]([C:11](=[O:16])[C:12]([C:13]([OH:15])=[O:14])=[CH:3][N:4]3[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])=[C:9]([CH3:17])[C:8]=2[F:18])[CH2:38]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 23364547HCID 23364547, compound

Product 1

HCID 14774111HCID 14774111, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.40 g (1.00 mmol) of ethyl 6,7,8-trifluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.22 g (1.18 mmol) of 3-t-butoxycarbonylaminopyrrolidine, 0.30 g (3.00 mmol) of triethylamine, and 15 ml of acetonitrile was refluxed for 18 hours. The mixture was cooled and concentrated. The residue was dissolved in 10 ml of 6N hydrochloric acid, refluxed for three hours, and cooled to room temperature. The solids were filtered, washed with water and ether, and suspended in water. The suspension was made basic (pH 12) and filtered through a fiberglass pad, and the filtrate was neutralized to pH 6.7. The solids were filtered and washed with water and ether to give 0.38 g of the title compound, mp 230°-232° C.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 10 ml of 6N hydrochloric acid
  4. temperaturerefluxed for three hours
  5. filtrationThe solids were filtered
  6. washwashed with water and ether
  7. filtrationfiltered through a fiberglass pad
  8. filtrationThe solids were filtered
  9. washwashed with water and ether

Sources & evidence

ORD record
ord-03b999c13e7a479ca161e33aae91b47e
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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