HCID 59807148, compound → HCID 178511876, compound

HRID 1922519Notes

Reaction equation

HRID 1922519 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][C:16]([NH2:20])=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)[CH2:3][CH2:2]1.I.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](SC)=[NH:28]>C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+]>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][C:16]([NH:20][C:27]([C:23]4[S:22][CH:26]=[CH:25][CH:24]=4)=[NH:28])=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 59807148HCID 59807148, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511876HCID 178511876, compoundYield 49.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred solution of 1-(3-morpholinopropyl)-1,2,3,4-tetrahydroquinolin-6-amine (190 mg, 0.690 mmol) in ethanol (10 ml) under argon was added methyl thiophene-2-carbimidothioate hydroiodide (393 mg, 1.380 mmol). The resulting suspension was then stirred overnight at room temperature. The mixture was then diluted with water and sodium carbonate and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in ethyl acetate, followed by 5-10% (2M NH3 in MeOH) in dichloromethane, giving the desired N-(1-(3-morpholinopropyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide 72 (132 mg, 0.343 mmol, 49.8% yield). 1H NMR (DMSO-d6) δ 7.67 (d, J=3 Hz, 1H), 7.56 (d, J=4.8 Hz, 1H), 7.09-7.06 (m, 1H), 6.56 (brs, 2H), 6.49 (s, 1H), 6.33 (brs, 2H), 3.60-3.56 (m, 4H), 3.26-3.17 (m, 4H), 2.66 (t, J=6.3 Hz, 2H), 2.34-2.28 (m, 6H), 1.89-1.81 (m, 2H), 1.69-1.63 (m, 2H). EI-MS (m/z, %) 384 (100, MH+), 270 (52). HPLC purity: 99%.

Workup

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

Sources & evidence

ORD record
ord-fe39c93bdd7d4eac9284432c6df242ad
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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