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phenyl 2-(6-amino-8-fluoro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate → HCID 178484205, compound

HRID 1922465
Notes
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Reaction equation

HRID 1922465 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]([CH2:13][CH2:14][N:15]([CH3:25])[C:16](=[O:24])[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7][CH2:6][CH2:5]2.I.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:32](SC)=[NH:33]>C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+]>[F:12][C:10]1[CH:11]=[C:2]([NH:1][C:32]([C:28]2[S:27][CH:31]=[CH:30][CH:29]=2)=[NH:33])[CH:3]=[C:4]2[C:9]=1[N:8]([CH2:13][CH2:14][N:15]([CH3:25])[C:16](=[O:24])[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7][CH2:6][CH2:5]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 59807114phenyl 2-(6-amino-8-fluoro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamateHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178484205HCID 178484205, compoundYield 75.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent
HCID 10340
Sodium Carbonate
Solvent

Procedure

To a stirred solution of phenyl 2-(6-amino-8-fluoro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate (426 mg, 1.241 mmol) in ethanol (12 ml) was added methyl thiophene-2-carbimidothioate hydroiodide (708 mg, 2.481 mmol). The reaction mixture was stirred at room temperature overnight under argon. The reaction mixture was then diluted with water and sodium carbonate, then extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in 40-100% ethyl acetate in hexanes, giving the desired phenyl 2-(8-fluoro-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate 52 (422 mg, 0.933 mmol, 75% yield). 1H NMR (DMSO-d6) δ 7.74-7.71 (m, 1H); 7.59-7.57 (m, 1H); 7.41-7.36 (m, 2H); 7.23-7.18 (m, 1H); 7.14-7.07 (m, 3H); 6.50-6.42 (m, 3H); 6.37 (s, 1H); 3.62 (t, J=6 Hz, 1H); 3.51 (t, J=6 Hz, 1H); 3.30 (t, J=6 Hz, 1H); 3.23 (t, J=6 Hz, 1H); 3.15-3.09 (m, 2H); 3.09, 2.97 (2s, 3H); 2.69 (t, J=6 Hz, 2H); 1.83-1.75 (m, 2H). EI-MS (m/z, %): 452 (M+, 8); 288 (60); 179 (100).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed in 40-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ee26eabd62b346d1950eb8946daf81a5
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173813B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes