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6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridine hydrochloride; In 1-ethoxyethanol; for 0.333333h;Heating / reflux; Alkaline conditions;
A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.166 g of <strong>[56354-98-4]6-amino-2-benzothiazolinone</strong>, 0.020 g of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 20 minutes. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrochloric acid to adjust pH to 7. The product was collected, washed with water, and dried to give 0.326 g of 6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile as a solid, mp 285-287C; mass spectrum (electrospray, m/e): M+H 379.0858.
Step B 6-Amino-1,3-benzothiazol-2(3H)-one The compound obtained in Step A (0.036 mol) is dissolved in 90 ml of methanol, and then 2.5 g of palladium-on-carbon and 18 g of ammonium formate are added in succession and the mixture is heated at reflux for 18 hours. 40 ml of dioxane are added and refluxing is continued for 24 hours. The palladium-on-carbon is then filtered off. The reaction mixture is concentrated, the resulting precipitate is filtered off, and the filtrate is evaporated under reduced pressure. The resulting residue is taken up in a 1N hydrochloric acid solution and extracted twice with 50 ml of ethyl acetate each time. The aqueous phase is rendered alkaline with a 10% potassium carbonate solution and extracted twice with 50 ml of ethyl acetate each time. The organic phase is dried and then evaporated under reduced pressure, and the resulting precipitate is recrystallized from acetonitrile. Melting point: 220-224 C.
5
[ 104-53-0 ]
[ 56354-98-4 ]
6-(3-phenylpropyl)amino-2-benzothiazolone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 8 6-(3-Phenylpropyl)amino-2-benzothiazolone By reaction of <strong>[56354-98-4]6-amino-2-benzothiazolone</strong> (1.66 g) with 3-phenylpropanal using the procedure of Example 1, the title compound (0.82 g) was prepared. m.p.: 145-149 C. IR(Nujol): 3400, 1650, 1610, 1590 cm-1. NMR (CDCl3): 1.70-2.20 (m, 2H), 2.50-3.30 (m, 4H), 4.10-4.50 (m, 1H), 6.30-7.00 (m, 3H), 7.20 (s, 5H), 10.70-11.20 (m, 1H).
6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With hydrogenchloride; pyridine hydrochloride; sodium carbonate; In water;
EXAMPLE 131 6,7-Dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.166 g of <strong>[56354-98-4]6-amino-2-benzothiazolinone</strong>, 0.020 g of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 20 minutes. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrochloric acid to adjust pH to 7. The product was collected, washed with water, and dried to give 0.326 g of 6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile as a solid, mp 285-287 C.; mass spectrum (electrospray, m/e): M+H 379.0858.
With sodium acetate; acetic acid; at 35 - 90℃; for 1.75h;
General procedure: 6-Amino-3H-1,3-benzoxazol-2-one (700 mg, 4.66 mmol) and sodium acetate (497 mg, 6.05 mmol) were dissolved in acetic acid (20 mL) at 35 C. Ethyl chlorooxoacetate (677 muL, 6.05 mmol) was added dropwise and the reaction mixture was stirred at 35 C for 1 h and 45 min at 90 C then water (50 mL) was added to the solution. The precipitate was filtered, washed with water (2 × 30 mL) and dried overnight under vacuum in presence of P2O5 to afford the intermediate ethyl 2-acetamido-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetate (857 mg, 74%) as a white solid. A solution of potassium hydroxide (101 mg, 1.80 mmol) in water (400 muL) was added to a suspension of ethyl 2-acetamido-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetate obtained above (150 mg, 0.60 mmol) in ethanol (3 mL) and the reaction mixture was stirred at room temperature for 2 h. Water (5 mL) was added to the mixture and the resulting homogenous solution was acidified to pH = 1 with concentrated HCl. The precipitate was filtered and dried overnight under vacuum in presence of P2O5 to give 4a (115 mg, 87%) as a white solid.
(RS)-ethyl 4-chloro-5, 6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate[ No CAS ]
[ 56354-98-4 ]
(RS)-ethyl 4-[(2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate HCl salt[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%
With hydrogenchloride; In 1,4-dioxane; ethanol; at 100℃; for 5h;
General procedure: A mixture comprising 1.00 g (3.37 mmol) (RS)-ethyl 4-chloro-5, 6,7,8- tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate which was prepared according to intermediate example 1a, 840 mg 6-amino-1 ,3-benzothiazol-2(3H)- one, 9.54 mL ethanol and 182 muIota_ hydrochloric acid (4M in dioxane) was reacted at 100C for 5 hours. The precipitate was washed with ethanol and diethyl ether and digested with hydrochloric acid (1M). After filtration the solid was washed with water, propan-2-ol, diethyl ether and dried to give 1.24 g (76%) of the title compound as hydrochloride.1H-NMR (DMSO-d6): delta= 1.18 (3H), 1.90 (1 H), 2.17 (1 H), 2.86-3.22 (5H), 4.09 (2H), 7.10 (1 H), 7.40 (1 H), 7.77 (1 H), 8.36 (1 H), 8.45 (1 H), 11.91 (1 H) ppm.
With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;
General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.
With hydrogenchloride; In 1,4-dioxane; ethanol; at 110℃; for 10h;
General procedure: A mixture comprising 60.0 mg (307 mumol) 4-chloro-6-ethyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (prepared according to intermediate exampLe 1a), 51 mg <strong>[56354-98-4]6-amino-1,3-benzothiazol-2(3H)-one</strong> (CAS-No: 56354-98-4), 1.75 mL ethanol and 16.9 muL hydrochloric acid (4M in dioxane) was reacted at 110C for 10 hours. The residue was digested in a mixture of diethyl ether and ethanol and dried to give 85.3 mg (85%) of the title compound.
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