Triethylamine → 1-Cyclopropyl-7-[3-(ethylaminomethyl)pyrrolidin-1-yl]-6-fluoro-4-oxo-8-(trifluoromethyl)quinoline-3-carboxylic acid

HRID 2107003Notes

Reaction equation

HRID 2107003 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:19])=[C:11](F)[C:12]=3[C:14]([F:17])([F:16])[F:15])[C:7](=[O:20])[C:6]([C:21]([OH:23])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.CC[N:26]([CH2:29][CH3:30])[CH2:27][CH3:28]>CC#N>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:19])=[C:11]([N:4]4[CH2:1][CH2:2][CH:30]([CH2:29][NH:26][CH2:27][CH3:28])[CH2:5]4)[C:12]=3[C:14]([F:15])([F:16])[F:17])[C:7](=[O:20])[C:6]([C:21]([OH:23])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 142788301-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-trifluoromethyl-3-quinolinecarboxylic acid

Product 1

HCID 30258041-Cyclopropyl-7-[3-(ethylaminomethyl)pyrrolidin-1-yl]-6-fluoro-4-oxo-8-(trifluoromethyl)quinoline-3-carboxylic acidYield 193.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylic acid (0.20 g, 0.61 mmol) 3-((N-ethylamino)methyl)pyrrolidine (0.20 g, 1.6 mmol) and NEt3 (0.20 g, 2 mmol) were refluxed with stirring under N2 in CH3CN (2 mL) for 2 hours. When the reaction mixture had cooled to 20° the yellow solid was collected by vacuum filtration, washed with water (5 mL) and ether (5 mL), and then dried at 110°/0.2 mm to give 1-cyclopropyl-7-(3-((N-ethylamino) methyl)pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylic acid (0.26 g, 97%) as a light yellow solid; mp 239°-241° C. C21H23N3O3F4 requires C, 57.14; H, 5.22; N, 9.52; F, 17.23%. Found, C, 56.77; H, 4.98; N, 9.34; F, 16.95%. Nmr (TFA) δ 9.37 (1 H, s, H 2), 8.02 (1 H, d, J=13.8 Hz, H 5), 7.2-7.5 (2 H, br s, NH+2), 4.45-4.55 (1 H, m, H 1 pyrrolidinyl), 4.1-4.4 (2 H, m, H 5 pyrrolidinyl), 3.9-4.1 (2 H, m, H 1 cyclopropyl +pyrrolidinyl, 3.3-3.65 (4 H, m, CH2s ethylaminomethyl), 2.9-3.1 (1 H, m, H 3 pyrrolidinyl), 2.5-2.65 (1 H, m, H 4 pyrrolidinyl), 1.9-2.1 (1 H, m, H 4 pyrrolidinyl), 1.5-1.8 (5 H, m and t, J=7.1 Hz, cyclopropyl and CH3), 0.95-1.4 (2 H, m, cyclopropyls). Ir (KBr) 1629, 1456, 1360 cm-1. MS 442 (4, M H⊕), 441 (4, M⊕).

Workup

  1. temperatureWhen the reaction mixture had cooled to 20° the yellow solid
  2. filtrationwas collected by vacuum filtration
  3. washwashed with water (5 mL) and ether (5 mL)
  4. customdried at 110°/0.2 mm

Sources & evidence

ORD record
ord-5eb8097b255d4c8f80c27e8f32fef456
Source dataset
uspto-grants-1990_06
Patent number
US04933335

Reaction notes

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