Triethylamine → HCID 14774111, compound

HRID 1081430Notes

Reaction equation

HRID 1081430 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 3 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 the resulting solution was 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 3 hours
  5. filtrationThe solids were filtered
  6. washwashed with water and ether
  7. filtrationthe resulting solution was filtered through a fiberglass pad
  8. filtrationThe solids were filtered
  9. washwashed with water and ether

Sources & evidence

ORD record
ord-e632a078dc4b439b9b8b17fdb2ab5e52
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

Loading…