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3-amino-N-{4-[(3R,4R,5S)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]pyridin-3-yl}-7-ethoxy-1,8-naphthyridine-2-carboxamide tris-trifluoroacetate[ No CAS ]
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4.0h;
A solution of LiAlH4 in THF (2.0 M, 1.7 mL, 3.4 mmol) was added dropwise to a solution of <strong>[1196157-51-3]2-amino-6-bromonicotinic acid</strong> (from Ark Pharm, 350 mg, 1.61 mmol) in anhydrous THF (8.2 mL) at 0 C., causing some effervescence. The solution was allowed to warm to ambient temperature gradually while stirring for 4 h. The reaction was quenched by the sequential addition of H2O (129 muL), 15% aq. NaOH (129 muL) and H2O (388 muL). The solution was stirred vigorously for 1 h, a precipitate was removed by filtration and the filtrate was concentrated under reduced pressure and used for the next reaction
1.55 g
With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 - 20℃;Inert atmosphere;
To <strong>[1196157-51-3]2-amino-6-bromonicotinic acid</strong> (2-Si, 2 g, 9.22 mmol) in THF (70 mL), LAH (1M in ether, 18.4 mL, 18.4 mmol) was added slowly at 0 C under argon with stirring. After completion of the addition, the ice bath was removed and the mixture was stirred at room temperature overnight. The reaction mixture was cooled again in an ice bath and saturated NH4C1 aqueous solution (25 mL) was added with stirring to form a slurry. The organic layer was separated by decantation and the slurry was washed with EtOAc. The combined organic layers were washed with iN NaOH aqueous solution and brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to afford (2-amino-6-bromopyridin-3-yl)methanol, (2-S2, 1.55 g)as a solid.
Step 1: 2-Amino-6-bromo-5-chloronicotinic acid N-Chlorosuccinimide (2.78 g, 20.8 mmol) was added to a solution of <strong>[1196157-51-3]2-amino-6-bromonicotinic acid</strong> (4.51 g, 20.8 mmol, Ark Pharm Inc. Arlington Heights, Ill., USA) in DMF (75 mL), and the resulting mixture was heated at 70 C. for 2.5 h. Heating was then stopped, and stirring was continued for 16 h. The reaction mixture was subsequently poured into ice water. After the ice had melted, the resulting slurry was filtered through a fritted glass funnel. The collected solids were air-dried, providing 2-amino-6-bromo-5-chloronicotinic acid: 1H NMR (400 MHz, DMSO-d6) delta 8.05 (s, 1H), 7.64 (br. s, 2H). m/z (ESI, +ve) 250.9 (M+H)+.
With N-chloro-succinimide; In N,N-dimethyl-formamide; at 70℃; for 2.5h;
N-Chlorosuccinimide (2.78 g, 20.8 mmol) was added to a solution of <strong>[1196157-51-3]2-amino-6-bromonicotinic acid</strong> (4.51 g, 20.8 mmol, Ark Pharm Inc. Arlington Heights, IL, USA) in DMF (75 mL), and the resulting mixture was heated at 70 C for 2.5 h. Heating was then stopped, and stirring was continued for 16 h. The reaction mixture was subsequently poured into ice water. After the ice had melted, the resulting slurry was filtered through a fritted glass funnel. The collected solids were air- dried, providing 2-amino-6-bromo-5-chloronicotinic acid: ?H NMR (400 MHz, DMSO-d6) oe 8.05 (s, 1H), 7.64 (br. s, 2H). m/z (ESI, +ve) 250.9 (M+H)
With N-chloro-succinimide; In N,N-dimethyl-formamide; at 70℃; for 2.5h;
Step 1: 2-Amino-6-bromo-5-chloronicotinic acid N-Chlorosuccinimide (2.78 g, 20.8 mmol) was added to a solution of <strong>[1196157-51-3]2-amino-6-bromonicotinic acid</strong> (4.51 g, 20.8 mmol, Ark Pharm Inc. Arlington Heights, Ill., USA) in DMF (75 mL), and the resulting mixture was heated at 70 C. for 2.5 h. Heating was then stopped, and stirring was continued for 16 h. The reaction mixture was subsequently poured into ice water. After the ice had melted, the resulting slurry was filtered through a fritted glass funnel. The collected solids were air-dried, providing 2-amino-6-bromo-5-chloronicotinic acid: 1H NMR (400 MHz, DMSO-d6) delta 8.05 (s, 1H), 7.64 (br. s, 2H). m/z (ESI, +ve) 250.9 (M+H)+.
(41R,43S,45R)-42-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-pyrazolo[3,4-c]pyridin-1-yl)acetyl)-16-bromo-8,8-dimethyl-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphane-3,7-dione[ No CAS ]
(41R,43S,45R)-16-bromo-8,8-dimethyl-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphane-3,7-dione trifluoroacetic acid salt[ No CAS ]
tert-butyl (41R,43S,45R)-16-bromo-8,8-dimethyl-3,7-dioxo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphane-42-carboxylate[ No CAS ]
tert-butyl (41R,43S,45R)-16-bromo-8,8-dimethyl-3,7-dioxo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphan-10-ene-42-carboxylate[ No CAS ]
(1R,3S,5R)-tert-butyl 3-(3-(allyloxymethyl)-6-bromopyridin-2-ylcarbamoyl)-5-((2,2-dimethylpent-4-enamido)methyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate[ No CAS ]
(41R,43S,45R)-42-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-pyrazolo[3,4-c]pyridin-1-yl)acetyl)-16-bromo-8,8-difluoro-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphane-3,7-dione[ No CAS ]
(41R,43S,45R)-42-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-16-bromo-8,8-difluoro-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphane-3,7-dione[ No CAS ]
(1R,20S,22R)-15-bromo-5,5-difluoro-10-oxa-3,16,18,21-tetraazatetracyclo[18.3.1.01,22.012,17]tetracosa-12,14,16-triene-4,19-dione trifluoroacetic acid salt[ No CAS ]
tert-butyl (41R,43S,45R)-16-bromo-8,8-difluoro-3,7-dioxo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphane-42-carboxylate[ No CAS ]
tert-butyl (41R,43S,45R,E)-16-bromo-8,8-difluoro-3,7-dioxo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphan-10-ene-42-carboxylate[ No CAS ]
tert-butyl (41R,43S,45R,E)-16-bromo-3,7-dioxo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphan-10-ene-42-carboxylate[ No CAS ]
(1R,3S,5R)-tert-butyl 3-((3-((allyloxy)methyl)-6-bromopyridin-2-yl)carbamoyl)-5-((2,2-difluoropent-4-enamido)methyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate[ No CAS ]
(10Z,31R,33S,35R)-32-(2-(3-acetyl-7-methyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-66-bromo-8-oxa-32,5-diaza-1(5,3)-oxadiazola-6(2,3)-pyridina-3(5,3)-bicyclo[3.1.0]hexanacycloundecaphan-10-en-4-one[ No CAS ]
(14Z,31R,33S,35R)-66-bromo-8-oxa-32,5-diaza-1(5,3)-oxadiazola-6(2,3)-pyridina-3(5,3)-bicyclo[3.1.0]hexanacycloundecaphan-10-en-4-one trifluoroacetic acid salt[ No CAS ]
tert-butyl (14Z,31R,33S,35R)-66-bromo-4-oxo-8-oxa-32,5-diaza-1(5,3)-oxadiazola-6(2,3)-pyridina-3(5,3)-bicyclo[3.1.0]hexanacycloundecaphan-10-ene-32-carboxylate[ No CAS ]
(41R,43S,45R,E)-42-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-16-bromo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphan-10-ene-3,7-dione[ No CAS ]
(1R,3S,5R)-tert-butyl 3-((3-((allyloxy)methyl)-6-bromopyridin-2-yl)carbamoyl)-5-((3-vinyl-1,2,4-oxadiazol-5-yl)methyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate[ No CAS ]
(41R,43S,45S,E)-42-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-16-bromo-6,11-dioxa-42,2-diaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclododecaphan-8-en-3-one[ No CAS ]
tert-butyl (41R,43S,45S,E)-16-bromo-3-oxo-6,11-dioxa-42,2-diaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclododecaphan-8-ene-42-carboxylate[ No CAS ]
(41R,43S,45R,E)-42-(2-(3-acetyl-7-(fluoromethyl)-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-16-bromo-11-oxa-42,2-diaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclododecaphan-8-en-3-one[ No CAS ]
(41R,43S,45S,E)-16-bromo-6,11-dioxa-42,2-diaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclododecaphan-8-en-3-one trifluoroacetic acid Salt[ No CAS ]
(41R,43S,45S)-42-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-16-bromo-6,11-dioxa-42,2-diaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclododecaphan-3-one[ No CAS ]
(31R,33S,35R)-32-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-66-bromo-11H-8-oxa-32,5-diaza-6(2,3)-pyridina-1(1,4)-triazola-3(5,3)-bicyclo[3.1.0]hexanacyclononaphan-4-one[ No CAS ]
tert-butyl (1R,3S,5R)-5-(azidomethyl)-3-((6-bromo-3-((prop-2-yn-1-yloxy)methyl)pyridin-2-yl)carbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate[ No CAS ]
(1R,3S,5R)-5-(azidomethyl)-N-(6-bromo-3-((prop-2-yn-1-yloxy)methyl)pyridin-2-yl)-2-azabicyclo[3.1.0]hexane-3-carboxamide trifluoroacetic acid salt[ No CAS ]
(1R,3S,5R)-2-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-5-(azidomethyl)-N-(6-bromo-3-((prop-2-yn-1-yloxy)methyl)pyridin-2-yl)-2-azabicyclo[3.1.0]hexane-3-carboxamide[ No CAS ]
N-((41R,43S,45R,8S)-42-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-16-bromo-3,7-dioxo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphan-10-en-8-yl)acetamide[ No CAS ]
tert-butyl (41R,43S,45R,8S)-8-acetamido-16-bromo-3,7-dioxo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphan-10-ene-42-carboxylate[ No CAS ]
N-((41R,43S,45R,8S)-16-bromo-3,7-dioxo-13-oxa-42,2,6-triaza-1(2,3)-pyridina-4(3,5)-bicyclo[3.1.0]hexanacyclotetradecaphan-10-en-8-yl)acetamide hydrochloride[ No CAS ]
tert-butyl (1R,3S,5R)-5-(((S)-2-acetamidopent-4-enamido)methyl)-3-((3-((allyloxy)methyl)-6-bromopyridin-2-yl)carbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate[ No CAS ]
(1R,19S,21R)-20-{2-[3-acetyl-5-(2-methylpyrimidin-5-yl)pyrazolo[3,4-c]pyridin-1-yl]acetyl}-14-bromo-7-methylidene-9-oxa-3,4,15,17,20-pentaazapentacyclo[17.3.1.13,6.01,21.011,16]tetracosa-4,6(24),11,13,15-pentaen-18-one[ No CAS ]
tert-butyl (1R,3S,5R)-3-({6-bromo-3-[(prop-2-en-1-yloxy)methyl]pyridin-2-yl}carbamoyl)-5-[(4-iodopyrazol-1-yl)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate[ No CAS ]
tert-butyl (1R,19S,21R)-14-bromo-7-methylidene-18-oxo-9-oxa-3,4,15,17,20-pentaazapentacyclo[17.3.1.13,6.01,21.011,16]tetracosa-4,6(24),11,13,15-pentaene-20-carboxylate[ No CAS ]
(1R,19S,21R)-14-bromo-7-methylidene-9-oxa-3,4,15,17,20-pentaazapentacyclo[17.3.1.13,6.01,21.011,16]tetracosa-4,6(24),11,13,15-pentaen-18-one trifluoroacetic acid salt[ No CAS ]
(1R,7E,20S,22R)-21-{2-[3-acetyl-5-(2-methylpyrimidin-5-yl)indazol-1-yl]acetyl}-15-bromo-10-oxa-3,16,18,21,25-pentaazapentacyclo[18.3.1.13,6.01,22.012,17]pentacosa-4,6(25),7,12,14,16-hexaen-19-one[ No CAS ]
tert-butyl (1R,3S,5R)-3-({6-bromo-3-[(prop-2-en-1-yloxy)methyl]pyridin-2-yl}carbamoyl)-5-[(3-ethenylpyrazol-1-yl)methyl]-2-azabicyclo[3.1.0]hexane-2-carboxylate[ No CAS ]
tert-butyl (1R,7E,20S,22R)-15-bromo-19-oxo-10-oxa-3,16,18,21,25-pentaazapentacyclo[18.3.1.13,6.01,22.012,17]pentacosa-4,6(25),7,12,14,16-hexaene-21-carboxylate[ No CAS ]
tert-butyl (1R,7Z,20S,22R)-15-bromo-19-oxo-10-oxa-3,16,18,21,25-pentaazapentacyclo[18.3.1.13,6.01,22.012,17]pentacosa-4,6(25),7,12,14,16-hexaene-21-carboxylate[ No CAS ]
(1R,7E,20S,22R)-15-bromo-10-oxa-3,16,18,21,25-pentaazapentacyclo[18.3.1.13,6.01,22.012,17]pentacosa-4,6(25),7,12,14,16-hexaen-19-one trifluoroacetic acid salt[ No CAS ]
With diazomethyl-trimethyl-silane In hexane; dichloromethane at 0 - 20℃;
1 1A. Methyl 2-amino-6-bromonicotinate
To a solution of 2-amino-6-bromonicotinic acid (1.00 g, 4.61 mmol) in a mixture of dichloromethane (30 mL) and methanol (15 mL) cooled to 0 °C was added trimethyl silyl diazomethane (2 M in hexane, 2.76 mL, 5.53 mmol) slowly. Once the addition was complete, the ice bath was removed, and the reaction mixture was allowed to warm to room temperature and stirred for 30 min. Analysis indicated that starting material was still present. An additional 1.2 mL of the trimethylsilyldiazomethane (2 M in hexane) was added, and the reaction was stirred overnight. The reaction mixture was concentrated and dried well under reduced pressure to give methyl 2-amino-6- bromonicotinate as a pale yellow solid. LC/MS [M+H]+ = 230.9 and 232.9.
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