* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Example 1; Preparation of intermediates N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide (1D) and N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(trifluoromethyl)benzamide (1E); Step A: Commercially available 6-bromopyridin-3-amine (1A, 20 g, 1.0 equivalent) was added in portions to a solution of potassium thiocyanate (5.0 equivalents) in acetic acid (0.4 M) at -5° C. After addition, the mixture was cooled to -15° C., and a solution of Br2 (1.3 equivalent) in acetic acic (9.4 M) was added drop wise via an additional funnel. The mixture was then warmed to room temperature and stirred for 12 h. The resulting precipitate was filtered; 100 mL EtOAc and 200 mL H2O were added to the filtrate and then 200 mL of solvent was removed in vacuo. The residue was stirred in ice bath for 10 minutes, and then the resulting precipitate was collected by filtration and washed twice with cold 10percent MeOH in Et2O. The filtrate was concentrated and the product was crystallized in ice bath to obtain a second crop of product after washing twice with cold 10percent MeOH in Et2O. The product 1B (77percent) was obtained as a brown solid after drying under vacuum, and then used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.94 (br. s., 1H) 7.44 (d, J=8.34 Hz, 1H) 7.57 (d, J=8.34 Hz, 1H) 8.04 (br. s., 1H); ESI-MS: m/z 230.0 (M+H)+.
68.93%
With bromine In acetic acid at 20℃; for 3.5 h;
Step 1: 5-bromothiazolo[5,4-b]pyridin-2-amine To a suspension of KSCN (2.2 g, 22.83 mmol) in acetic acid (10 ml) was added 6-bromopyridin-3-amine (1 g, 5.78 mmol) and the mixture was stirred at room temperature for 15 min. A solution of bromine (0.38 ml 7.51 mmol) in acetic acid (10 ml) was added dropwise to the obtained solution at room temperature for 15 min. After the completion of dropwise addition the mixture was stirred at room temperature for 3 h. Reaction was monitored by TLC. On completion to the reaction mixture was added water (25 ml); the solid so precipitated was filtered out. The filtrate was concentrated under reduced pressure; the residue was neutralised to pH=7 with aq. sol. of NaHCO3 and extracted with mixture of THF:ethyl acetate (1:1). The organic layer was dried over sodium sulphate, concentrated under reduced pressure to afford 5-bromothiazolo[5,4-b]pyridin-2-amine (0.910 g, 68.93percent) as reddish brown solid. MS: 231.86[M++1]
61%
With bromine In acetic acid at -15 - 20℃; Inert atmosphere
Example 1; Preparation of 7V-(5-Bromothiazolo[5,4-Z>]pyridin-2-yl)acetamide (1); 1A 1B Example 1[0376] To a 500 ml 3-neck under N2 was added KSCN (42.1 g, 433 mmol), followed by 225 mL of HOAc. It was cooled to -5 0C and 6-bromo-3-aminopyridine (15 g, 86.7 mmol) was added in portions. The mixture was further cooled to -15 0C, and a solution of Br2 (5.7 mL) in 12 mL of HOAc was added dropwise while keeping the bath temperature below 10 0C. It was then allowed to slowly warm up to room temperature and stirred overnight. The small amount of precipitate was filtered off. The mother liquor was cooled to 0 0C, and water was added (200 mL). It was stirred for 5 min, and the precipitate formed was collected and washed with cold MeOH/Et2O (1 :3, 50 mL, 2 times). The solid was dried under vacuum overnight to give 5-bromothiazolo[5,4-b]pyridin-2- amine the titled compound as a yellow solid (10.2 g, 51percent). The solvent was stripped from the filtrate to half the volume, and the precipitation was collected, washed with cold MeOH-Et2O, and dried to give another 2 g of product with a combined yield of 12.2 g (61percent yield).
As shown in step 4-ii of Scheme 21, Compound 1005 (5.44 g, 20 mmol) was suspended in 6 N HCl (100 mL). The reaction mixture was heated at reflux for 1 h, at which time all of the material went into solution. The mixture was cooled to RT and the reaction was made basic to a pH of 10, at which time the product precipitated out. The solid was collected on a fritted funnel and dried to afford 5-bromothiazolo[5,4-δ]pyridin-2-amine (Compound 1006, 4.35 g, 93percent yield): ESMS (M+H) 230, 232; 1H NMR (DMSO-d6) δ 7.9 (br, 2H), 7.6 (d, IH), 7.4 (d, IH).
Reference：
[1] Yakugaku Zasshi, 1951, vol. 71, p. 662,665[2] Chem.Abstr., 1952, p. 8109
6
[ 4487-59-6 ]
[ 934266-82-7 ]
Reference：
[1] Yakugaku Zasshi, 1951, vol. 71, p. 662,665[2] Chem.Abstr., 1952, p. 8109
7
[ 934266-82-7 ]
[ 108-24-7 ]
[ 1112982-76-9 ]
Yield
Reaction Conditions
Operation in experiment
100%
at 20℃;
Example 1; Preparation of 7V-(5-Bromothiazolo[5,4-Z>]pyridin-2-yl)acetamide (1); 1A 1B Example 1[0376] To a 500 ml 3-neck under N2 was added KSCN (42.1 g, 433 mmol), followed by 225 mL of HOAc. It was cooled to -5 0C and 6-bromo-3-aminopyridine (15 g, 86.7 mmol) was added in portions. The mixture was further cooled to -15 0C, and a solution of Br2 (5.7 mL) in 12 mL of HOAc was added dropwise while keeping the bath temperature below 10 0C. It was then allowed to slowly warm up to room temperature and stirred overnight. The small amount of precipitate was filtered off. The mother liquor was cooled to 0 0C, and water was added (200 mL). It was stirred for 5 min, and the precipitate formed was collected and washed with cold MeOH/Et2O (1 :3, 50 mL, 2 times). The solid was dried under vacuum overnight to give 5-bromothiazolo[5,4-b]pyridin-2- amine the titled compound as a yellow solid (10.2 g, 51percent). The solvent was stripped from the filtrate to half the volume, and the precipitation was collected, washed with cold MeOH-Et2O, and dried to give another 2 g of product with a combined yield of 12.2 g (61percent yield). To the above obtained compound (11.3 g, 40 mmol) in pyridine (88 mL) was slowly added Ac2O (44 mL) at 0 0C. The mixture was then stirred at room temperature for 16 h. Solvent was removed, and the residue was subjected to vacuum for 20 h to give N- (5-bromothiazolo[5,4-b]pyridin-2-yl)acetamide as a light brown solid (13.3 g, 100percent). [M+H] calc'd for C8H6BrN3OS, 272; found, 272.
80%
With dmap In dichloromethane at 20℃; Cooling with ice; Inert atmosphere
In a similar manner as for 5b, started with 4b (0.25 g, 1.09 mmol) to produce 5d (0.23 g, 80percent). Mp: 240.0-242.0 °C; 1H NMR (DMSO-d6): δ 12.62 (s, 1H, NH), 8.16 (d, J = 8.8 Hz, 1H, Ar-H), 7.57 (d, J = 8.8 Hz, 1H, Ar-H), 2.24 (s, 3H, CH3). ESI-HRMS m/z: calcd for C8H6BrN3NaOS [M+Na]+: 293.9313; found 293.9315.
Reference：
[1] Patent: WO2010/8847, 2010, A2, . Location in patent: Page/Page column 123
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3739 - 3748
To a mixture of title compound E, 3-Cyclopentyl-2-[4-(4-methyl-piperazine-1-sulfonyl)- phenyl]-propionic acid (5.Og, 10.7 mmol), HOBt (2.8g, 20.7 mmol) and EDC (4.1g, 20.7 mmol) in 100 mL of DMF at 00C was added 5.3 mL of DIEA, and the mixture is stirred for 30 min prior to addition of 5-Bromo-thiazolo[5,4-b]pyridin-2-yl amine (2.4g, 10.7mmol). The reaction mixture is stirred at ambient temperature for 18 h and then quenched into brine and extracted with ethyl acetate. The combined extracts were washed with 1N NaOH, brine and then dried over MgSO4. Filtration and evaporation then afforded a brownish foam which is purified by chromatography over silica to provide title compound F: 1H NMR (400 MHz, DMSO-D6) ? ppm 1.06-1.17 (m, 2 H) 1.3 (s, 9 H) 1.37-1.46 (m, 2 H) 1.5-1.6 (m, 4 H) 1.68 (m, 2H) 1.77-1.84 (m, 1 H) 2.8 (m, 4 H) 3.4 (m, 4H) 4.1 (t, 1 H J = 8.4 Hz) 7.65-7.68 (m, 4 H) 7.72 (d, 1 H, J = 8.5 Hz) 9.04 (d, 1 H, J =8.5 Hz) 12.9 (m, 1 H); ? 1. MS 680 [M+1]+, 678[M-I]",
With triethylamine;dmap; In tetrahydrofuran; at 20℃; for 5h;
As shown in step 4-iii of Scheme 21, Compound 1006 (1.5 g, 6.5 mmol) was dissolved in THF (100 mL), and triethylamine (1.2 mL, 8.48 mmol) and DMAP (80 mg, 0.65 mmol) were added. Di-tert-buty dicarbonate (2.0 g, 8.47 mmol) was added and the reaction was stirred at RT for 5 h. The solvent was removed under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with very slightly acidic water (75 mL H2O/5 mL 1 N HCl) and brine, dried over Na2SO4, and concentrated under reduced pressure. The product was triturated with DCM to afford tert- butyl 5-bromothiazolo[5,4-delta]pyridin-2-ylcarbamate (Compound 1007, 1.65 g, 76% yield) as a white solid: ESMS (M-H) 328, 330; 1H NMR (DMSO-d6) delta 12.08 (s, IH), 7.99 (d, IH), 7.64 (d, IH), 1.52 (s, 9H).
60%
With dmap; In Petroleum ether;
Step 2: tert-Butyl 5-bromothiazolo[5,4-b]pyridin-2-ylcarbamate To a suspension of <strong>[934266-82-7]5-bromothiazolo[5,4-b]pyridin-2-amine</strong> (15.0 g, 65.1 mmol) in DCM (300 mL) was added di-tert butyl dicarbonate (21.0 g, 96.2 mmol) and 4-dimethylaminopyridine (8 g, 65.5 mmol). The reaction mixture stirred at room temperature for 2 h and evaporated in vacuo. The residue was purified via flash chromatography on silica gel (solvent gradient: 0-50% ethyl acetate in petroleum ether) to yield 13 g (60%) of the title compound as a white solid. LCMS (ESI): [M+H]+=330/332.
10.5%
With triethylamine;dmap; In acetone; at 50℃;
Step 2; To a solution of 58 (3.98 g, 17.3 mmol), Boc2O (4.91 g), and triethylamine (2.5 g) in acetone (50 mL), DMAP (84 mg) was added. The solution was heated to 50C and stirred overnight, and then concentrated. The residue was purified by column chromatography to yield target compound 59 (2.81 g, y. 10.5%).
As shown in step 4-ii of Scheme 21, Compound 1005 (5.44 g, 20 mmol) was suspended in 6 N HCl (100 mL). The reaction mixture was heated at reflux for 1 h, at which time all of the material went into solution. The mixture was cooled to RT and the reaction was made basic to a pH of 10, at which time the product precipitated out. The solid was collected on a fritted funnel and dried to afford 5-bromothiazolo[5,4-delta]pyridin-2-amine (Compound 1006, 4.35 g, 93% yield): ESMS (M+H) 230, 232; 1H NMR (DMSO-d6) delta 7.9 (br, 2H), 7.6 (d, IH), 7.4 (d, IH).
Example 6; Preparation of N-(5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)nicotinamide (6); Step A: <strong>[934266-82-7]5-bromothiazolo[5,4-b]pyridin-2-amine</strong> (1B, 200 mg, 1.0 equivalent) and nicotinoyl chloride hydrochloride (6A, 2.0 equivalents) was added pyridine (0.17 M) and was stirred at room temperature for 12 h. The solvent was removed in vacuo, and MeOH/Et2O was added to the residue and cooled in ice bath for 10 minutes. The resulting precipitate was collected by filtration and washed twice with cold 10% MeOH in Et2O to afford compound 6B (70%) as a white solid: ESI-MS: m/z 335.0 (M+H)+.
In N,N-dimethyl acetamide; at 50℃; for 12h;Inert atmosphere;
Step B: 4-acetylbenzoyl chloride (3B, 560 mg, 1.0 equivalent) was dissolved in DMA (0.15 M). Methyl 4-(chlorocarbonyl)benzoate (2.0 equivalent) was then added. The mixture was heated to 50 C. for 12 h, followed by addition of water and extraction with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography (SiO2, gradient of 5 to 20% EtOAc/Hex) to give 3C (16%) as a tan solid: 1H NMR (400 MHz, DMSO-d6) delta ppm 2.66 (s, 3 H) 7.73 (d, J=8.59 Hz, 1H) 8.08-8.17 (m, 3H) 8.25 (d, J=8.84 Hz, 2H) 13.36 (br. s., 1H); ESI-MS: m/z 376.0 (M+H)+.
In N,N-dimethyl acetamide; at 50℃; for 7h;Inert atmosphere;
Example 4; Preparation of intermediates N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-tert-butylbenzamide (4A) and 4-tert-butyl-N-(5-chlorothiazolo[5,4-b]pyridin-2-yl)benzamide (4B); <strong>[934266-82-7]5-bromothiazolo[5,4-b]pyridin-2-amine</strong> (1B, 1.0 g, 1.0 equivalent) was dissolved in DMA (0.36 M), and then 4-tert-butylbenzoyl chloride (2.0 equivalents) was added. The mixture was heated to 50 C. under N2 for 7 h. After cooling to room temperature, the crude mixture was added saturated aqueous NaHCO3 and extracted with EtOAc three times. Combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (SiO2, gradient of 5 to 20% EtOAc/hexanes) to give 4A (44%) as a white solid: 1H NMR (400 MHz, DMSO-d6) delta ppm 1.33 (s, 9H) 7.61 (d, J=8.34 Hz, 2H) 7.72 (d, J=8.34 Hz, 1H) 8.10 (dd, J=8.34, 3.03 Hz, 3H) 13.08 (s, 1H); ESI-MS: m/z 390.0 (M+H)+.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 150℃; for 3h;Inert atmosphere; Microwave irradiation;
Example 5; Preparation of N-(5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-cyclopropylbenzamide (5); Step A: To a microwave vial, <strong>[934266-82-7]5-bromothiazolo[5,4-b]pyridin-2-amine</strong> (1B, 100 mg, 1.0 equivalent), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5A, 2.0 equivalent), Na2CO3 (4.0 equivalents), DMF (0. 15 M) and H2O (0.73 M) were added. While mixture was under N2, Pd(PPh3)4 was added and the mixture was then heated in a microwave for 3 h at 150 C. The crude mixture was filtered, and purified by preparatory LCMS. Intermediate 5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine (5B) was obtained as a white solid. ESI-MS: m/z 218.0 (M+H)+.
In N,N-dimethyl acetamide; at 50℃; for 1h;Inert atmosphere;
Step B: <strong>[934266-82-7]5-bromothiazolo[5,4-b]pyridin-2-amine</strong> (1B, 5.0 g, 1.0 equivalent) was dissolved in DMA (0.9 M), and then followed by addition of methyl 4-(chlorocarbonyl)benzoate (2.0 equivalent). The mixture was then heated to 50 C. for 1 h. After the mixture was cooled to room temperature, a 70 mL solution of 5% MeOH in Et2O was added. After stirring for 10 minutes, the resulting fine precipitate was collected by filtration. The filtered caked was taken into a 150 mL solution of 30% MeOH in Et2O, and stirred at 30 C. for 10 minutes. The mixture was then filtered and the collected solid was washed twice with cold solution of 10% MeOH in Et2O. After drying under vacuum, the product 1C (60%) was obtained as a light yellow solid, and was used in the next step without further purification. 1C: 1H NMR (400 MHz, DMSO-d6) delta ppm 3.89 (s, 3H) 7.67-7.74 (m, 1H) 8.05-8.14 (m, 3H) 8.22 (d, J=8.84 Hz, 2H) 13.33 (br. s., 1H); ESI-MS: m/z 392.0 (M+H)+.
Step D: 4-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)benzoic acid (2D, 3.0 g, 1.0 equivalent) was dissolved in DMF, then followed by addition of TBTU (1.2 equivalent). The mixture was stirred at room temperature for 2 h, then <strong>[934266-82-7]5-bromothiazolo[5,4-b]pyridin-2-amine</strong> (1.2 equivalent) was added, and followed by Et3N (3.0 equivalents), and this was heated to 60 C. for 12 h. After stirring, water was added and followed by extraction with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (SiO2, gradient of 5 to 10% EtOAc/hexanes) to give 2E (60%) as a white solid: ESI-MS: m/z 520.0 (M+H)+.
Example 1; Preparation of 7V-(5-Bromothiazolo[5,4-Z>]pyridin-2-yl)acetamide (1); 1A 1B Example 1[0376] To a 500 ml 3-neck under N2 was added KSCN (42.1 g, 433 mmol), followed by 225 mL of HOAc. It was cooled to -5 0C and 6-bromo-3-aminopyridine (15 g, 86.7 mmol) was added in portions. The mixture was further cooled to -15 0C, and a solution of Br2 (5.7 mL) in 12 mL of HOAc was added dropwise while keeping the bath temperature below 10 0C. It was then allowed to slowly warm up to room temperature and stirred overnight. The small amount of precipitate was filtered off. The mother liquor was cooled to 0 0C, and water was added (200 mL). It was stirred for 5 min, and the precipitate formed was collected and washed with cold MeOH/Et2O (1 :3, 50 mL, 2 times). The solid was dried under vacuum overnight to give 5-bromothiazolo[5,4-b]pyridin-2- amine the titled compound as a yellow solid (10.2 g, 51%). The solvent was stripped from the filtrate to half the volume, and the precipitation was collected, washed with cold MeOH-Et2O, and dried to give another 2 g of product with a combined yield of 12.2 g (61% yield). To the above obtained compound (11.3 g, 40 mmol) in pyridine (88 mL) was slowly added Ac2O (44 mL) at 0 0C. The mixture was then stirred at room temperature for 16 h. Solvent was removed, and the residue was subjected to vacuum for 20 h to give N- (5-bromothiazolo[5,4-b]pyridin-2-yl)acetamide as a light brown solid (13.3 g, 100%). [M+H] calc'd for C8H6BrN3OS, 272; found, 272.
80%
With dmap; In dichloromethane; at 20℃;Cooling with ice; Inert atmosphere;
In a similar manner as for 5b, started with 4b (0.25 g, 1.09 mmol) to produce 5d (0.23 g, 80%). Mp: 240.0-242.0 C; 1H NMR (DMSO-d6): delta 12.62 (s, 1H, NH), 8.16 (d, J = 8.8 Hz, 1H, Ar-H), 7.57 (d, J = 8.8 Hz, 1H, Ar-H), 2.24 (s, 3H, CH3). ESI-HRMS m/z: calcd for C8H6BrN3NaOS [M+Na]+: 293.9313; found 293.9315.
With triethylamine; In dichloromethane;Cooling with ice; Inert atmosphere;
In a similar manner as for 5c, started with 4b (0.30 g, 1.62 mmol) to produce 5e (0.35 g, 72%). Mp: >270 C; 1H NMR (DMSO-d6): delta 12.94 (s, 1H, NH), 8.16 (d, J = 8.8 Hz, 1H, Ar-H), 7.57 (d, J = 8.8 Hz, 1H, Ar-H), 2.03 (m, 1H, CH), 0.99 (m, 4H, CH2). ESI-HRMS m/z: calcd for C10H8BrN3OS [M+H]+: 297.9650; found 297.9659.
54%
With triethylamine; In dichloromethane; at 70℃;
Example 9; Preparation of 7V-(5-(6-Chloro-5-(methylsulfonamido)pyridin-3- yl)thiazolo [5,4-6] pyridin-2-yl)cyclopropanecarboxamide (9); Me [0384] To IB (5 g, 21.6 mmol) in CH2Cl2 (220 mL) was slowly added triethylamine (37.6 mL) and cyclopropanecarbonylchloride (9 mL). The mixture was then refluxed at 70 0C for 1 h. The solvent was removed, and the crude product was crystallized from EtOH to give 9 A as a white solid (3.5 g, 54%).
General procedure: Step A: 5-Fluorothiazolo[5,4-b] A three-neck flask was fitted with a mechanical stirrer and charged with potassium rhodanate (25.1 g, 258 mmol) and acetic acid (81 mL). The suspension was stirred at 0 C while 6-methoxypyridin-3 -amine (4.00 g, 32.2 mmol) was added. A solution of bromine (5.15 mL, 100 mmol) in acetic acid (27 mL) was added over 30 min via an addition funnel. After bromine addition was complete, the ice-water bath was removed and the reaction mixture was allowed to warm to ambient temperature and was stirred at that temperature for 16 h. Water (30 mL) was added to the reaction mixture and it was placed into a preheated oil-bath and stirred at 85 C for 20 min. The solids were filtered hot, collected, and recrystallized from methanol to afford 5-fluorothiazolo[5,4-b]pyridin-2-amine (2.38 g, 13.1 mmol, 41 % yield) as a yellow solid.
19
[ 934266-82-7 ]
[ 1440428-02-3 ]
Yield
Reaction Conditions
Operation in experiment
In a similar manner as for compound 8a, started with compound 4b to produce compound 7b as crude product which was used for the next step directly, then following the procedure to prepare 8a and using compound 7b (0.5g, 2.0mmol) to produce 8b (0.35g, 77%).
Step 1: 5-Bromothiazolo[5,4-b]pyridin-2-amine To a suspension of 6-bromopyridin-3-amine (20.0 g, 115 mmol) and potassium thiocyanate (56.0 g, 576 mmol) in acetic acid (250 mL) was added dropwise a solution of bromine (23.88 g, 149 mmol) in acetic acid (100 mL) at room temperature. The reaction mixture was stirred at room temperature for 15 h. The solids were filtered out, and then the resulting solution was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (solvent gradient: 0-10% methanol in DCM) to yield 18 g (68%) of the title compound. LCMS (ESI): [M+H]+=230/232.
Step 2: Synthesis of 5-bromo-2-chlorothiazolo[5,4-b]pyridine To a stirred solution of <strong>[934266-82-7]5-bromothiazolo[5,4-b]pyridin-2-amine</strong> (0.5 g, 2.17 mmol) in ACN (8 ml) was added CuCl2 (0.432 g, 3.21 mmol)at 0 C. reaction allowed to run at 0 C. for 15 min. After 15 min. tBuONO (0.38 mL, 3.21 mmol) dissolved in ACN (2 ml) was added to reaction mixture at 0 C., its stir at room temperature for 16 h. Reaction was monitored of TLC. On completion reaction mixer was concentrated under reduced pressure. To the residue was added water and reaction mixer extracted with ethyl acetate. The organic layer was washed with water, saturated aq. sol. of NaHCO3 brine, dried over sodium sulphate and concentrated under reduced pressure to afford of 5-bromo-2-chlorothiazolo[5,4-b]pyridine (0.470 g, 87.03%) as yellow solid. MS: 250.74[M++1]
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