Triethylamine → HCID 14555456, compound

HRID 232039Notes

Reaction equation

HRID 232039 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.[CH3:21][C:22]([O:25][C:26](=[O:38])[NH:27][CH:28]([CH3:37])[C:29](=[O:36])[NH:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)([CH3:24])[CH3:23].C(N(CC)CC)C>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:33]4[CH2:34][CH2:35][CH:31]([NH:30][C:29](=[O:36])[CH:28]([NH:27][C:26]([O:25][C:22]([CH3:24])([CH3:23])[CH3:21])=[O:38])[CH3:37])[CH2:32]4)[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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 14555449tert-Butyl {(S)-1-methyl-2-oxo-2-[(S)-pyrrolidin-3-ylamino]ethyl}carbamate

Product 1

HCID 14555456HCID 14555456, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.4 g (50 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1.92 g (7.5 mmol) of [1-methyl-2-oxo-2-[(3-pyrrolidinyl)amino]ethyl]-carbamic acid 1,1-dimethylethyl ester, 1.5 g (15 mmol) of triethylamine and 75 ml of acetonitrile was heated at reflux for five hours. The solvent was removed in vacuo and the residue was partitioned between chloroform/water (250 ml each) and acidified to pH 2.0 at 0° with 6.0M hydrochloric acid. The solid was removed by filtration, washed with water and dried in vacuo to give 2.4 g of the title compound, mp 185°-187°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for five hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between chloroform/water (250 ml each)
  5. customacidified to pH 2.0 at 0° with 6.0M hydrochloric acid
  6. customThe solid was removed by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-dcfd98a4680c43989f1d8e9661ad8142
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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