* 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.
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 18 h; Heating / reflux Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0℃;
a) 3,4-Dihydro-2H-pyrido[3,2-][l,4]oxazine; To an ice-cold solution of 4H-ρyrido[3,2-][l,4]oxazin-3-one (5.00 g, 33.3 mmol) in TηF (40 mL) was added lithium aluminum hydride (66.6 mL of a 1.0 M solution in TηF, 66.6 mmol). Following the addition, the solution was heated to reflux. After 18 h, the solution was cooled to 00C and quenched the reaction with H&2O (4 mL) followed by NaOH (4 mL, 15percent) and H2O (10 mL). The resulting slurry was filtered over Celite and the filtrate concentrated to give the title compound (3.87 g, 85percent) as a blue-gray powder: 1H NMR (500 MHz, OMSO-d6) δ 7.53 (dd, J= 4.5, 1.0 Hz, IH), 6.90-6.89 (m, IH), 6.61 (br s, IH), 6.44 (dd, J= 8.0, 3.0 Hz, IH), 4.08 (t, J= 4.5 Hz, 2H), 3.39-3.36 (m, 2H); MS (ESI) m/e \\31 (M + η)\\
79%
With sodium hydroxide; LiAlH4 In tetrahydrofuran
a) 3,4-Dihydro-2H-pyrido[3,2-b]-1,4-oxazine To a suspension of 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (2.0 g, 13.3 mmole) in dry THF (40 mL) was added a solution of LiAlH4 in THF (1.0 M, 26.6 mL, 26.6 mmole) slowly at 0°C. After 1 hr the mixture was quenched with 2.0 M NaOH until a solid formed. The mixture was dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (1.44 g, 79percent) as a white solid which was sufficiently pure for use in the next step: MS (ES) m/e 137 (M + H)+.
With sodium hydrogencarbonate In water; butanone at 20 - 75℃; for 1.5 h; Cooling with ice
2-Amino-3-ol (45 mmol) and sodium hydrogen carbonate (51 mmol) in water (30 ml) and 2-butanone (30 ml) mixed solution. Under ice-cooling, chloroacetyl chloride (51 mmol) of 2-butanone (10 ml) was slowly added, maintaining the temperature during the addition does not exceed 10 ° C. It was stirred at room temperature for 30 minutes, stirring for 1 hour at 75 ° C, and concentrated recrystallization (methanol / water = 1: 1) to give 4.3 g of the title compound.
Reference：
[1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 2, p. 133 - 142
[2] Helvetica Chimica Acta, 1976, vol. 59, p. 1593 - 1612
[3] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0605-0607
3
[ 1268818-15-0 ]
[ 20348-09-8 ]
Yield
Reaction Conditions
Operation in experiment
77%
for 2.5 h; Inert atmosphere; Reflux
General procedure: To a stirred solution of 2a (2 mmol) in acetic acid (10 mL), powdered Fe (12 mmol) was added and the reaction mixture was then refluxed for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and the acetic acid was removed under reduced pressure, EtOAc (20 mL) was added and was stirred for 2 min and then filtered to remove any iron impurities. The insoluble iron residue was washed with EtOAc (20 mL). The filtrate and washings were combined and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the crude product thus obtained was purified by column chromatography to obtain the pure product 3a.
To a solution of compound 15 (1 g, 6.66 mmol) in DMF (30 mL) was added dropwise bromine (0.480 mL, 9.32 mmol). The reaction mixture was stirred overnight at room temperature. Water was added and a precipitate was formed which was collected by filtration and dried in lyophilizer overnight to afford title compound 16 (1.16 g, 76percent yield). IH NMR <n="95"/>(DMSO-d6) δ (ppm): 11.43 (s, IH), 8.04 (d, J = 2.0 Hz, IH), 7.65 (d, J = 2.0 Hz, IH), 4.67 (s,2H).
69%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 72 h;
a) 7-Bromo-2H-pyrido[3,2-jb][1 ,4]oxazin-3(4H)-oneA mixture of 2H-pyrido[3,2-d][1 ,4]oxazin-3(4H)-one (1.30 g, 8.66 mmol) and N-bromosuccinimide (1.70 g, 9.53 mmol) in DMF (30 mL) was stirred for three days at room temperature . Water (10 mL) was added and the suspension was cooled EPO <DP n="58"/>with an ice bath. The resulting precipitate was filtered, washed with water, and air- dried in a Buchner funnel to give the title compound (1.37 g, 69percent) as a white solid.MS(ES+) m/e 229 [M+H]+.
260 mg
With bromine In N,N-dimethyl-formamide at 20℃; for 2 h;
the step A compound (3.24mmol) was dissolved in 14 ml of N, N- dimethylformamide, then slowly added Bromine(3.56 mmol). At room temperature it wasstirred for 2 hours then water (300 ml) wasadded .the resulting precipitate was collected by filtration then it was washed with water and dried to give 260 mg ofthe title compound.
Reference：
[1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 2, p. 133 - 142
[2] Patent: WO2009/100536, 2009, A1, . Location in patent: Page/Page column 93-94
[3] Patent: WO2006/113432, 2006, A2, . Location in patent: Page/Page column 56-57
[4] Patent: US4906629, 1990, A,
[5] Patent: US4822794, 1989, A,
[6] Patent: US4866074, 1989, A,
[7] Patent: WO2004/14384, 2004, A2, . Location in patent: Page/Page column 256; 262
[8] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0608-0610
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 5h;
To a mixture of step-2 Intermediate (0.18 g, 1.20 mmol) and potassium carbonate (0.25 g, 1.8 mmol) in DMF (5 mL) was added methyl iodide (0.11 mL, 1.8 mmol). The resulting mixture was stirred at room temperature for 5 h. The reaction was then diluted with water (10 mL) and the resultant solid obtained was filtered, washed with water (10 mL) and dried to afford 100 mg (51%) of the title compound as white solid. 1HNMR (400 MHz, CDCl3) delta 8.05 (d, J=5.0 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 6.96 (d, J=5.0 Hz, 1H), 4.70 (s, 2H), 3.50 (s, 3H); GC-MS (m/z) 164 (M)+.
To a solution of compound 15 (1 g, 6.66 mmol) in DMF (30 mL) was added dropwise bromine (0.480 mL, 9.32 mmol). The reaction mixture was stirred overnight at room temperature. Water was added and a precipitate was formed which was collected by filtration and dried in lyophilizer overnight to afford title compound 16 (1.16 g, 76% yield). IH NMR <n="95"/>(DMSO-d6) delta (ppm): 11.43 (s, IH), 8.04 (d, J = 2.0 Hz, IH), 7.65 (d, J = 2.0 Hz, IH), 4.67 (s,2H).
69%
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 72h;
a) 7-Bromo-2H-pyrido[3,2-jb][1 ,4]oxazin-3(4H)-oneA mixture of 2H-pyrido[3,2-d][1 ,4]oxazin-3(4H)-one (1.30 g, 8.66 mmol) and N-bromosuccinimide (1.70 g, 9.53 mmol) in DMF (30 mL) was stirred for three days at room temperature . Water (10 mL) was added and the suspension was cooled EPO <DP n="58"/>with an ice bath. The resulting precipitate was filtered, washed with water, and air- dried in a Buchner funnel to give the title compound (1.37 g, 69%) as a white solid.MS(ES+) m/e 229 [M+H]+.
With N-Bromosuccinimide; In water; N,N-dimethyl-formamide;
Step 1. 7-Bromo-2H-pyrido[3,2-b]1,4-oxazin-3(4H)-one To a solution of 5.6 g 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one dissolved in 85 ml of DMF under nitrogen is added 7.96 g NBS in 50 ml of DMF. This is allowed to stir at room temperature overnight. To this is added 35 ml of water and the mixture is chilled The solid material which separates is filtered and washed with 3*100 ml H2 O. This is then dried under vacuum at 70 C. and then used directly in the next step.
With N-Bromosuccinimide; In water; N,N-dimethyl-formamide;
Step 1. 7-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one To a solution of 5.6 g 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one dissolved in 85 ml of DMF under nitrogen is added 7.96 g NBS in 50 ml of DMF. This is allowed to stir at room temperature overnight. To this is added 35 ml of water and chilled. The solid material which separates is filtered and washed with 3*100 ml H2 O. This is then dried in a vac oven at 70 C. and then used directly in the next step.
With N-Bromosuccinimide; In water; N,N-dimethyl-formamide;
Step 1. 7-Bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one To a solution of 5.6 g <strong>[20348-09-8]2H-pyrido[3,2-b]-1,4-oxazin-3-(4H)-one</strong> dissolved in 85 ml of DMF under nitrogen is added 7.96 g NBS in 50 ml of DMF. This is allowed to stir at room temperature overnight. To this is added 35 ml of water and chilled. The solid material which separates is filtered and washed with 3*100 ml H2 O. This is then dried in a vac oven at 70 C. and then used directly in the next step.
With bromine; In DMF (N,N-dimethyl-formamide);
In Scheme 90c, the oxazine (24) can be prepared from compound (22) using a similar strategy previously used for (21). Base catalyzed addition of (22) to [CHLOROACETIC] acid followed by cyclization affords intermediate (22). Compound (22) can undergo halogenation using bromine in an aprotic solvent such as DMF to give compound (24).
260 mg
With bromine; In N,N-dimethyl-formamide; at 20℃; for 2h;
the step A compound (3.24mmol) was dissolved in 14 ml of N, N- dimethylformamide, then slowly added Bromine(3.56 mmol). At room temperature it wasstirred for 2 hours then water (300 ml) wasadded .the resulting precipitate was collected by filtration then it was washed with water and dried to give 260 mg ofthe title compound.
65.30 g
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 50℃; for 20h;
To 2H-pyrido[3,2-b][1 ,4]oxazin-3(4H)-one (45.0 g, 300 mmol) in DMF (360 mL) at 20 C was added NBS (74.7 g, 420 mmol) in one portion, and the resulting brownish suspension was heated at 50 C for 20 hours. The mixture was cooled to 25 C, and the content was poured into stirred water (1 L) in a 3 L flask fitted with an overhead mechanical stirrer. The resulting aqueous suspension was stirred at room temperature for 30 minutes followed by filtration. The yellowish cake was washed with 10% Na2S203 solution (100 mL) followed by water (2 x 100 mL). The cake was aspirated at room temperature under house vacuum overnight. The solids were washed with Et20 (100 mL), aspirated under house vacuum at room temperature for 18 hours, and then dried under high vacuum at 50 C for 72 hours to afford the title compound (65.30 g) as a light tan-colored powdery solid. LC-MS (ES) m/z = 229, 231 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 4.68 (s, 2H), 7.66 (d, J = 2.0 Hz, 1 H), 8.02 (d, J = 2.0 Hz, 1 H), 1 1 .44 (br. s., 1 H).
With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; acetone; at 20℃; for 48h;
1 IA. 5-Oxy-4H-pyridor3.2-biri.41oxazin-3-one; <n="140"/>m-Chloroperbenzoic acid (2.76 g, 16.0 mmol) was added in portions to a stirred suspension of 4H-pyrido[3,2-b][l,4]oxazin-3-one (2 g, 13.3 mmol) in a mixture of ethyl acetate (150 mL) and acetone (100 mL) at room temperature. After stirring at room temperature for 2 days, a fine precipitate was formed. The solid was collected, washed with acetone and dried in vacuo, to yield 5-oxy-4H-pyrido[3,2-b][l,4]oxazin-3-one (1.9 g, 86%) as a light grey powder. LC-MS (LCT2) m/z 167.1[MMI+], R, 1.69 min. 1H (500 MHz, d6-DMSO) delta 8.00 (IH, dd, J = 6.3, 1.4 Hz), 7.10-6.95 (2, m), 4.72 (2H, s
With acetic anhydride; triethylamine; for 72h;Heating / reflux;
Benzaldehyde (1.59 g, 0.016 mol) was added to a mixture of 2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (1.50 g, 0.01 mol), acetic anhydride (4 ml) and triethylamine (2 ml). The reaction mixture was refluxed for 72 h, then cooled to room temperature. The precipitated solid was collected by filtration, washed with acetonitrile and purified by silica gel chromatography using (8:2) toluene:ethyl acetate.
Sodium methoxide (0.65 g, 0.012 mol) was added in one portion to a mixture of 2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (1.50 g, 0.01 mol) and pyrrole-2-carboxaldehyde (1.58 g, 0.016 mol) in dry DMF (10 ml). The reaction mixture was refluxed for 48 h, then cooled to room temperature, poured into crushed ice and left overnight at 4 C. The precipitated solid was filtered off, washed with water and dried. The dark solid was boiled with ethanol (150 ml) and filtered hot to remove impurities. The filtrate was evaporated to dryness under reduced pressure, and the residue was purified by silica gel chromatographed using (95:5) toluene:ethyl acetate as the mobile phase.
In Scheme 90c, the oxazine (24) can be prepared from compound (22) using a similar strategy previously used for (21). Base catalyzed addition of (22) to [CHLOROACETIC] acid followed by cyclization affords intermediate (22). Compound (22) can undergo halogenation using bromine in an aprotic solvent such as DMF to give compound (24).
With sodium hydride; In hexanes; N,N-dimethyl-formamide; at 120℃; for 2h;
D1 was prepared according to Savelon et al, Bioorg. Med. Chem. 1998, 6, 133. To a slurry of D1 (301 mg, 2.0 mmol) in DMF (3 mL) was added NaH 60% in hexanes (92 mg, 2.30 mmol) followed by p-fluorobenzyl bromide (472 mg, 2.5 mmol). The reaction was stirred for 2 h at 120 C, then cooled and poured into brine and EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to afford 372 mg (72%) of D2.
With iron; acetic acid; for 2.5h;Inert atmosphere; Reflux;
General procedure: To a stirred solution of 2a (2 mmol) in acetic acid (10 mL), powdered Fe (12 mmol) was added and the reaction mixture was then refluxed for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and the acetic acid was removed under reduced pressure, EtOAc (20 mL) was added and was stirred for 2 min and then filtered to remove any iron impurities. The insoluble iron residue was washed with EtOAc (20 mL). The filtrate and washings were combined and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the crude product thus obtained was purified by column chromatography to obtain the pure product 3a.
With sulfuric acid; nitric acid; at 20℃; for 0.75h;
(Example 4 Synthesis of Compounds I-112, I-108, I-120, and 1-124) [Show Image][Show Image]Step 1 To a commercially available compound (11) (5.00 g, 33.3 mmol) in concentrated sulfuric acid (16.5 mL), concentrated sulfuric acid (3.5 mL) and nitric acid (3.5 mL, 84.0 mmol) were added dropwise at room temperature over 15 minutes. The solution, as it is, was then stirred for 30 minutes. The reaction solution was then poured to ice. The precipitated powder was filtered, washed with water, and then dried to yield subject compound (12) (3.12 g, 48%) as a pale yellow powder.1H-NMR (DMSO-d6) 511.66 (1H, s), 7.73 (1H, d, J = 8.7 Hz), 7.38 (1H, d, J = 8.7 Hz), 4.60 (2H, s).
With potassium carbonate; In N,N-dimethyl-formamide; at 50 - 110℃;
To a solution of cis-3-(((benzyloxy)carbonyl)amino)cyclobutyl 4-methylbenzenesulfonate (0.563 g, 1.5 mmol) in DMF (3.00 ml) was added 2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (FSSI, 0.225 g, 1.500 mmol) and potassium carbonate (EMD, 0.415 g, 3.00 mmol). The resulting mixture was heated to 50 C. overnight. Reaction mixture was heated to 85 C. for 3 hr then at 110 C. overnight. Reaction mixture was diluted with DCM and washed with water and brine. Purification by Biotage (0-10% MeOH/DCM) produced product. Material was advanced to the next step. M+1: 353.9
2-(4-(tert-butoxycarbonylamino)-2-oxabicyclo[2.2.2]octan-1-yl)ethyl methanesulfonate[ No CAS ]
tert-butyl 1-(2-(3-oxo-2H-pyrido[3,2-b][1,4]oxazin-4(3H)-yl)ethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84.0 mg
EXAMPLE 1096-((l-(2-(3-Oxo-2H-pyrido[3,2-b][l,4]oxazin-4(3H)-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylamino)methyl)-2H-pyrido[3,2-b][l,4]oxazin-3(4H)-oneHydrochlorideStep 1tert-Butyl 1 -(2-(3-Oxo-2H-pyrido[3,2-b] [ 1 ,4]oxazin-4(3H)-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylcarbamateTo a suspension of sodium hydride (38.0 mg, 55%) in N,N-dimethylacetamide (5 mL) was added 2H-pyrido[3,2-b][l,4]oxazin-3(4H)-one (151 mg) under cooling with ice, the mixture was stirred at room temperature for 30 minutes. The mixture was added AC (151 mg) under cooling with ice, the mixture was stirred at room temperature for 1.5 hours and further stirred at 60 C for 4 hours. The mixture was concentrated in vacuo. After dilution of the residue with ethyl acetate, the mixture was added saturated ammonium chloride solution under cooling with ice. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, chloroform : ethyl acetate = 2: 1) of the residue gave tert-butyl l-(2-(3-oxo-2H-pyrido[3,2-b][l,4]oxazin- 4(3H)-yl)ethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate (84.0 mg).1H NMR (CDC13): delta 1.42 (s, 9H), 1.69-2.10 (m, 10H), 3.90 (s, 2H), 4.16-4.29 (m, 3H), 4.62 (d, J= 3.7 Hz, 2H), 6.90 (dd, J= 8.0, 4.9 Hz, 1H), 7.19 (dd, J= 7.3, 1.2 Hz, 1H), 8.01 (dd, J= 4.8, 1.2, Hz, 1H).MS (ESI+) m/z: 404 (MH+).HRMS (ESI+) for C2iH3oN305 (MH+): calcd, 404.21855; found, 404.21800.
4-[2-(trimethylsilyl)ethoxy]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Step A. 4- { F2-(Trimethvlsilvl)ethoxvlmethvl} -2H-pyridoF3 ,2-b] F 1,4] oxazin-3 (411)-one Sodium hydride (60% dispersion in mineral oil; 0.48 g, 12 mmol) is added inportions to a solution of 2H-pyrido[3,2-b][1,4]oxazin-3(4R)-one (1.50 g, 10 mmol) in DMF (20 mL) at 0 C and the mixture is stirred for 1 h. 2-(Trimethylsilyl)ethoxymethylchloride (2.1 mL, 12 mmol) is added slowly dropwise and the mixture is then stirred at ambient temperature for 1h. The reaction is quenched by pouring into ice-water and the mixture is then extracted with CH2C12 (3 x). The combined organic extracts are washed with brine, dried (MgSO4), filtered andconcentrated in vacuo. The crude product is purified by silica gel chromatography (gradient elution with hexanes-EtOAc) to afford the title compound.
6-bromo-3-(chloromethyl)-2-methylimidazo[1,2-a]pyridine[ No CAS ]
4-[(6-bromo-2-methylimidazo[1,2-a]pyridin-3-yl)methyl]-2H,3H,4H-pyrido[3,2-b][1,4]-oxazin-3-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
18%
With caesium carbonate; 5-(N,N-dimethyl)amiloride hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 16h;
To a stirred solution of 2H,3H,<strong>[20348-09-8]4H-pyrido[3,2-b][1,4]oxazin-3-one</strong> (316 mg, 2.10mmol) in dry DMA (10.5 mL) was added caesium carbonate (2.74 g, 8.40 mmol). To the mixture was added Intermediate 6(551 mg, 2.10 mmol) in dry DMF (10.5 mL) dropwise. The reaction mixture was stirred at room temperature for 16 h. The residue was dissolved in ethyl acetate (15 mL) and water (15 mL). The aqueous layer was further extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (15 mL)and dried over sodium sulphate, then the solvents were removed in vacuo. The crude residue was purified on silica (Biotage, 25 g), eluting with 0 -80% ethyl acetate in heptane followed by 20% methanol in dichloromethane. A further purification using preparative HPLC afforded the title compound (150 mg, 18%). H (250 MHz, DMSO-d6) 9.00-8.89 (br s, 1H), 8.03 (dd, J4.8, 1.4 Hz, 1H), 7.44-7.35 (m, 2H), 7.30 (dd, J9.5, 1.8 Hz, 1H),7.07 (dd,J7.9, 4.8 Hz, 1H), 5.53 (s, 2H), 4.82(s, 2H), 2.43 (s, 3H). LCMS m/z373/375.
2-chloro-N-(3-hydroxypyridin-2-yl)acetamide[ No CAS ]
[ 20348-09-8 ]
Yield
Reaction Conditions
Operation in experiment
71%
With potassium carbonate; In N,N-dimethyl-formamide; at 75℃; for 1.5h;
To a solution of step-1 Intermediate (0.50 g, 1.88 mmol) in DMF (10 mL) was added potassium carbonate (0.52 g, 3.77 mmol) at room temperature. The resulting mixture was then stirred at 75 C. for 1.5 h. The reaction was then cooled to room temperature, diluted with water (15 mL) and ethyl acetate (15 mL). The aqueous layer was extracted with ethyl acetate (2×15 mL) and the combined organic layers were washed with water (2×20 mL), brine (20 mL), dried (Na2SO4) and filtered. The filtrate was concentrated on rotary evaporator and the crude product was purified by flash column chromatography (silica gel, 30% ethyl acetate in hexane system as eluent) to afford 200 mg (71%) of the title product as a white solid. 1HNMR (400 MHz, DMSO-d6) delta 11.25 (s, 1H, D2O exchangeable), 7.89 (dd, J=5.0 & 1.5 Hz, 1H), 7.34 (dd, J=8.0 & 1.5 Hz, 1H), 6.97 (dd, J=8.0 & 5.0 Hz, 1H), 4.64 (s, 2H); GC-MS (m/z) 150 (M)+.
2-(4-ethyl-3-methyl-3,4-dihydro-2 H-pyrido[3,2-b][1,4]oxazin-7-yl)-1-((2-ethyloxazol-4-yl)methyl)-N-methyl-1H-benzo[d]imidazole-5-carboxamide[ No CAS ]
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