8-Fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178480161, compound

HRID 1922478Notes

Reaction equation

HRID 1922478 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])[CH2:9][CH2:8][CH2:7]2.I.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](SC)=[NH:28]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:20][C:27]([C:23]2[S:22][CH:26]=[CH:25][CH:24]=2)=[NH:28])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 598070738-Fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178480161HCID 178480161, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 8-fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine (580 mg, 2.091 mmol) in ethanol (15 ml) was added methyl thiophene-2-carbimidothioate hydroiodide (1193 mg, 4.18 mmol) as a solid. The resulting suspension was stirred overnight at room temperature under argon. The reaction mixture was then quenched with water and sodium carbonate (sat) and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated. The residue was then chromatographed in ethyl acetate, followed by 0-10% (2M NH3 in methanol) in dichloromethane, giving the desired N-(8-fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (485 mg, 1.255 mmol, 60.0% yield). 1H NMR (DMSO-d6) δ 7.71 (d, J=3 Hz, 1H), 7.57 (d, J=4.5 Hz, 1H), 7.07 (dd, J=4.8, 3.9 Hz, 1H), 6.44 (brs, 2H), 6.39-6.34 (m, 2H), 3.07-3.02 (m, 4H), 2.95-2.89 (m, 1H), 2.69-2.65 (m, 2H), 2.21 (s, 3H), 2.03-1.99 (m, 2H), 1.94-1.87 (m, 2H), 1.76-1.74 (m, 2H), 1.63-1.59 (m, 2H), 1.46-1.40 (m, 2H).

Workup

  1. customThe reaction mixture was then quenched with water and sodium carbonate (sat)
  2. extractionextracted with dichloromethane (3×)
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then chromatographed in ethyl acetate

Sources & evidence

ORD record
ord-5c5f51e374cf47828c44b166a08b2427
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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