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PREPARATION 86 4-Methylindole-2-carboxylic acid (I) Following the general procedure of PREPARATION 63 and making non-critical variations but starting with methyl 4-methylindole-2-carboxylate (PREPARATION 85, 4.94 g), potassium hydroxide (1.75 g), the title compound is obtained, NMR (300 MHz, CD3 OD) 7.24, 7.19, 7.12, 6.85 and 2.51 delta.
1-(ethyl)-3-(dimethylaminopropyl)carbodiimide[ No CAS ]
[ 18474-57-2 ]
[ 147539-21-7 ]
1-[4-Methylindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2pyridinyl]piperazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 97 1-[4-Methylindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2pyridinyl]piperazine (III) Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with <strong>[18474-57-2]4-methylindole-2-carboxylic acid</strong> (PREPARATION 86, 0.40 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.50 g) and 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide (0.52 g), the title compound is obtained, mp 165-167.
[4-([1-(3-amidino-benzyl)-4-methyl-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium trifluoroacetate trifluoroacetic acid salt[ No CAS ]
[4-([1-(3-amidino-benzyl)-4-methyl-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-benzyl-dimethyl-ammonium trifluoroacetate trifluoroacetic acid salt[ No CAS ]
With copper(I) oxide; potassium phosphate; In 1-methyl-pyrrolidin-2-one; at 160℃; for 12h;Inert atmosphere; Schlenk technique;
General procedure: A mixture of Cu2O (0.02 mmol), K3PO4 (0.4 mmol), indole-2-carboxylic acid (1) (0.2 mmol), and aryl halide (2) (0.2 mmol) in NMP (2.0 mL) was stirred at room temperature under a N2 atmosphere. The mixture was then heated to 160 C and stirred at this temperature for 12 h. After completion of the reaction, the mixture was cooled to room temperature and diluted with EtOAc. The mixture was washed with H2O and aq NaCl, dried over MgSO4 and filtered. After evaporation of the solvent, the residue was purified by preparative thin-layer chromatography on silica gel with PE/EtOAc (50:1) as eluent to give the product 3.
4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylamine dihydrochloride[ No CAS ]
5-(4-methyl-1H-indole-2-carbonyl)-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
18%
To a solution of <strong>[18474-57-2]4-methyl-1H-indole-2-carboxylic acid</strong> (0.0356 g, 0.203 mmol) and 4,5,6,7- tetrahydrothiazolo[5,4-c]pyridin-2-amine dihydrochioride (0.03 00 g, 0.132 mmol) in DMF (1 mL) was added triethylamine (0.134 mL, 0.96 mmol). The mixture was stirred for 15 mins,then cooled (ice bath). EDCI (0.0408 g, 0.213 mmol) and HOAt (0.0026 mg, 0.019 mmol) were added. The mixture was slowly warmed to r.t. and stirred for 24h. The mixture was diluted with MeOH (0.5 mL) and MeCN (2 mL), filtered, and the filtrate purified by basic HPLC to give the desired product (0.0110 g, 18% yield).Rt (Method A) 3.02 mins, m/z 313 [M+Hj.