1-(3-(Pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178511875, compound

HRID 1922527Notes

Reaction equation

HRID 1922527 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27]>C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+]>[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([NH:19][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 533923491-(3-(Pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511875HCID 178511875, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred solution of 1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine (115 mg, 0.443 mmol) in ethanol (6 ml) under argon was added methyl thiophene-2-carbimidothioate hydroiodide (253 mg, 0.887 mmol). The reaction mixture was 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 on silica gel using ethyl acetate, followed by 5-10% (2M NH3 in methanol) in dichloromethane as eluent to give the desired N-(1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (119 mg, 0.323 mmol, 72.8% yield). 1H NMR (DMSO-d6) δ 7.67 (d, J=3.6 Hz, 1H), 7.55 (d, J=5 Hz, 1H), 7.06 (dd, J=5, 3.6 Hz, 1H), 6.58 (brs, 2H), 6.48 (s, 1H), 6.27 (brs, 2H), 3.26-3.17 (m, 4H), 2.66 (t, J=6.3 Hz, 2H), 2.45-2.40 (m, 6H), 1.89-1.81 (m, 2H), 1.70-1.62 (m, 6H). ESI-MS (m/z, %) 369 (MH+, 47), 185 (100). ESI-HRMS calculated for C21H29N4S (MH+), calculated: 369.2122, observed: 369.2107. HPLC purity: >95%.

Workup

  1. extractionextracted with dichloromethane (3×)
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-5bb0a14e29c84768aac5257bf172c6ad
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…