Reaktion #42949

Reaktionsgleichung

aluminum

(6,7-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

ethyl bromopyruvate

MgSO4

→

2-[1-(tert-butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-ylamino]thiazole-4-carboxylic acid ethyl ester

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepreheated to 60° C.
2. 2
   TemperaturThe reaction was cooled
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue was purified

Vorschrift

A solution of (6,7-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (50 mg, 0.127 mmol) and ethyl bromopyruvate (30.4 mg, 0.140 mmol) in acetone (1.4 mL) in a conical vial was added MgSO4 (7.7 mg, 0.0637 mmol). The resulting suspension was placed in an aluminum block preheated to 60° C. and was allowed to stir for 3.0 h. The reaction was cooled and concentrated. The residue was purified using a 5 g silica cartridge (MeOH/CH2Cl2, 1:99) to give 2-[1-(tert-butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-ylamino]thiazole-4-carboxylic acid ethyl ester as a pale yellow solid (42.2 mg; 68%). 1H-NMR (CDCl3): δ, 8.51 (s, 1H), 7.48 (s, 1H), 7.42 (s, 1H), 6.13 (s, 1H), 4.91 (d, 2H, J=4.7 Hz), 4.39 (q, 2H, J=7.0 Hz), 4.05 (s, 3H), 3.99 (s, 3H), 1.50 (s, 9H), 1.40 (t, 3H, J=7.3 Hz); MS: calculated for C23H28N4O6S+H 489.0; found: 489.0.

Quelle