Reaktion #42970

Reaktionsgleichung

N-benzylmethylamine

Triethylamine

thiophosgene

solution

2-(4-Amino-6,8-dimethoxy-isoquinolin-1-ylmethyl)-isoindole-1,3-dione

→

title compound

Ausbeute 39.0%

3-(1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-1-benzyl-1-methyl-thiourea

Ausbeute 39.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction stirred for 1 h
2. 2
   SonstigeSolvent was removed in vacuo
3. 3
   workup.STIRRINGstirring for 1 h
4. 4
   SonstigePurification by Prep-HPLC

Vorschrift

Triethylamine (46 μL, 0.33 mmol) and then thiophosgene (13 μL, 0.16 mmol) were added to a solution of Example 45C (40 mg, 0.11 mol) in dichloromethane (3 mL), and the reaction stirred for 1 h at r.t. N-benzylmethylamine (46 μL, 0.33 mmol) was added, and the reaction stirred for 1 h. Solvent was removed in vacuo, and the residue was deprotected with a solution of hydrazine (0.1 mL) in ethanol (4 mL), stirring for 1 h. Purification by Prep-HPLC gave 18 mg (39%) of the title compound (TFA salt) as a yellow solid. H1-NMR (MeOD-d4): δ 8.15 (s, 1H), 7.22-7.38 (m, 5H), 6.70 (s, 1H), 6.66 (s, 1H), 5.18 (s, 2H), 4.58 (s, 2H), 3.96 (s, 3H), 3.81 (s, 3H), 3.23 (s, 3H). MS (ES) (M+H) calc'd for C21H24N4O2S, 397; found 397.

Quelle