Diisopropylethylamine → HCID 59286546, compound

HRID 1876033Notes

Reaction equation

HRID 1876033 reaction equation
[Cl-].[NH3+:2][CH2:3][C@@:4]1([OH:12])[CH:9]2[CH2:10][CH2:11][NH+:6]([CH2:7][CH2:8]2)[CH2:5]1.[Cl-].CCN(C(C)C)C(C)C.[Cl:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[CH:30]=[N:29][C:28]([N:36]=[C:37]=[S:38])=[CH:27]2>CN(C=O)C>[Cl:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[CH:30]=[N:29][C:28]([NH:36][C:37]([NH:2][CH2:3][C@@:4]1([OH:12])[CH:9]3[CH2:8][CH2:7][N:6]([CH2:11][CH2:10]3)[CH2:5]1)=[S:38])=[CH:27]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59286551HCID 59286551, compoundHCID 178478858HCID 178478858, compound

Product 1

HCID 59286546HCID 59286546, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirring suspension of (S)-3-(ammoniomethyl)-3-hydroxy-1-azoniabicyclo[2.2.2]octane chloride (111 mg, 0.484 mmol) in DMF (3 mL) was added Hunig's Base (0.5 mL, 2.86 mmol) and the resulting mixture was stirred at room temperature for 35 minutes. Then was added a suspension of 6-chloro-3-isothiocyanato-7-methoxyisoquinoline (106 mg, 0.423 mmol) in DMF (3 mL) and the reaction mixture was allowed to stir at room temperature overnight. The solvent was evaporated in vacuo and the residue subjected to a silica gel column in 1% NH4OH/9% MeOH/90% CHCl3 to give 140.3 mg (82%) as a white solid, (S)-1-(6-chloro-7-methoxyisoquinolin-3-yl)-3-((3-hydroxyquinuclidin-3-yl)methyl)thiourea. LCMS RT 1.28 min, MH+=407.1, 409.0, 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 11.85 (1H, t, J=5.2 Hz), 9.15 (1H, br. s.), 8.63 (1H, s), 7.76 (1H, s), 6.92 (1H, s), 6.89 (1H, s), 4.14 (1H, dd, J=13.9, 5.6 Hz), 3.99 (2H, s), 3.90 (1H, dd, J=14.0, 5.2 Hz), 3.46 (3H, s), 2.89-3.01 (2H, m), 2.75-2.88 (3H, m), 2.03-2.15 (1H, m), 1.89-1.96 (1H, m), 1.77-1.88 (1H, m), 1.63 (1H, ddd, J=13.4, 6.1, 3.4 Hz), 1.32-1.45 (1H, m).

Workup

  1. additionThen was added
  2. stirringto stir at room temperature overnight
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-73d5e025e588421395bdecfe36ef99e7
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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