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CAS No. : | 40332-16-9 | MDL No. : | MFCD00956879 |
Formula : | C9H8N2O2 | Boiling Point : | 406.3°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 176.17 g/mol | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In chloroform; acetone for 6h; Heating; | |
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride | ||
With sodium hydroxide In ethanol for 0.25h; Heating; | ||
With potassium hydroxide In water; acetone Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-carbodiimide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With thionyl chloride In chloroform; acetone for 8h; Heating; | |
With oxalyl dichloride for 5h; Ambient temperature; | ||
With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 1h; | 2 To a solution of (1H-benzimidazol-1-yl)acetic acid (1 g, 5.68 mmol) (Example 1B) in N,N-dimethylformamide (25 mL) was added thionyl chloride (0.4 mL, 5.56 mmol) drop-wise and the reaction mixture stirred at room temperature for 1 h. 6-Phenyl-pyridin-2-ylamine (5.46 mmol) and pyridine (4 mL) were then added to the reaction mixture and stirred at room temperature for 17 h. The reaction mixture was then concentrated in vacuo and dichloromethane was added and transferred to a separating funnel where the organics were washed with 0.1M hydrochloric acid and 10% ammonium hydroxide solution. The organic layers were combined and washed with saturated aqueous sodium chloride, dried (Mg2SO4), filtered and concentrated in vacuo. The residue was then purified by column chromatography using silica and eluding with 0-10% methanol in dichloromethane, affording the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 5.29 (2H, s), 7.28-7.35 (2H, m), 7.39-7.48 (3H, m), 7.54 (1H, d, J=7.2 Hz), 7.62 (1H, d, J=7.7 Hz), 7.71 (1H, d, J=7.3 Hz), 7.81 (1H, t, J=7.9 Hz), 7.98 (1H, br d), 8.05 (2H, d, J=7.3 Hz), 8.23 (1H, s). MS (ES) m/z: 329.1 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5h; | |
76% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 5h; | 11 This example demonstrates a synthesis of benzotriazol-1-yl-ethanol (93) used in the preparation of compounds in an embodiment of the invention. See Figure 3. [0123] Procedure used for the preparation of 93 from 91 is similar to those used for the preparation of 92 from 90; amorphous solid, the yield is 59 %. 1H NMR (CDCl3) δ (IH, d with small coupling, J= 8.5 Hz), 7.61 (IH, d with small coupling, J= 8.2 Hz), 7.50 (IH, ddd, J= 1.1, 7.0 and 8.1 Hz), 7.36 (IH, ddd, J= 1.2, 6.9 and 8.1 Hz), 4.75 (2H, t, J= 5.1 Hz), 4.25 (2H, dd, J= 5.9 and 10.3 Hz), 2.55 (IH, t, J= 6.0 Hz); HRMS (ESI-MS m/z) calcd for C8Hi0N3O 164.0824 found 164.0812. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 76 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / 20 °C 2: 88 percent / iodine; imidazole; triphenylphosphine / diethyl ether; acetonitrile / 2 h / 0 °C 3: 51 percent / Cs2CO3 / dimethylformamide / 20 °C 4: 57 percent / NH3 / ethanol / 110 - 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 76 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / 20 °C 2: 88 percent / iodine; imidazole; triphenylphosphine / diethyl ether; acetonitrile / 2 h / 0 °C 3: 51 percent / Cs2CO3 / dimethylformamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 76 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / 20 °C 2: 88 percent / iodine; imidazole; triphenylphosphine / diethyl ether; acetonitrile / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 58 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 54 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 48 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 50 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 45 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 48 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 43 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 45 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 46 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 49 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 42 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 40 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / SOCl2 / CHCl3; acetone / 8 h / Heating 2: 41 percent / 4N aq. KOH / acetone / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 62 percent / copper(II) bronze / xylene / 17 h / 90 °C 2: 1 N NaOH / ethanol / 0.25 h / Heating | ||
Multi-step reaction with 2 steps 1: ethanolic sodium ethylate 2: aqueous HCl | ||
Multi-step reaction with 2 steps 1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / acetone / Reflux 2: potassium hydroxide / water; acetone / Reflux |
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 12 h / 0 - 25 °C 2: hydrogenchloride; water / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl chloride / 5 h / Ambient temperature 2: 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With hydrogen In methanol at 20℃; for 14h; | 45 To a stirred solution of benzimidazol-1-ylacetic acid benzyl ester (1.25 g, 4.69 mmol) in methanol (30 mL) was added 10% palladium on carbon (130 mg). The resultant reaction mixture was subjected to hydrogenation using a balloon full of hydrogen at room temperature for 14 h. This was filtered through a pad of Celite, the Celite pad was washed with excess methanol, and the combined filtrate was concentrated to get benzimidazol-1-ylacetic acid (0.4 g, 48% yield). NMR (300 MHz, DMSO-d6): δ 8.18 (s, 1H), 7.65 (d, J=8.51 Hz, 1H), 7.52 (d, J=8.24 Hz, 1H), 7.17-7.27 (m, 2H), 5.13 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: 4-(3,4-difluorophenyl)-1,3-thiazol-2-amine; 2-(1H-benzo[d]imidazol-1-yl)acetic acid With triethylamine In ethyl acetate at 20℃; for 1h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 24h; Stage #3: With sodium carbonate In water; ethyl acetate | 3.B (1H-Benzimidazol-1-yl)acetic acid (3.1 g, 0.017 mol) (Example 1B) was dissolved in ethyl acetate. Triethylamine (9 mL, 0.064 mmol) then added followed by 4-(3,4-difluorophenyl)-thiazol-2-ylamine (Example 3A) (3.7 g, 0.017 mol) and stirred at room temperature for 1 h. 50% wt. propylphosphonic anhydride solution in ethyl acetate (PPA) (10.8 mL, 0.017 mol) was then added dropwise and the mixture stirred for 24 h at room temperature. The mixture was then partitioned between ethyl acetate and sodium carbonate solution and washed with sodium carbonate (3×100 mL). The organics were combined, dried (MgSO4), filtered and evaporated to dryness. The solid was then triturated with methanol to afford a white solid (3.1 g, 48%). 1H NMR (400 MHz, CD3OD) δ ppm 5.65 (2H, s), 7.28 (1H, dd, J=8.4 and 18.9 Hz), 7.47 (1H, s), 7.66-7.74 (3H, m), 7.79-7.84 (1H, m), 7.88-7.94 (2H, m), 9.49 (1H, s). MS (ES) m/z: 371.2 [M+H]. |
48% | With triethylamine In ethyl acetate at 20℃; for 1h; | 3.B B: 2-benzimidazol-1-yl-N-r4-(3,4-difluorophenyl)-thiazol-2-yll-acetamide (1 H-Benzimidazol-1-yl)acetic acid (3.1g, 0.017mol) (Example IjJ) was dissolved in ethyl acetate. Triethylamine (9ml_, 0.064mmol) then added followed by 4-(3,4-difluoro- phenyl)-thiazol-2-ylamine (Example 3A) (3.7g, 0.017mol) and stirred at room temperature for 1h. 50% wt. propylphosphonic anhydride solution in ethyl acetate (PPA) (10.8ml_, 0.017mol) was then added dropwise and the mixture stirred for 24h at room temperature. The mixture was then partitioned between ethyl acetate and sodium carbonate solution and washed with sodium carbonate (3 x 10OmL). The organics were combined, dried (MgSO4), filtered and evaporated to dryness. The solid was then triturated with methanol to afford a white solid (3.1g, 48%). 1H NMR (400MHz, CD3OD) δ ppm 5.65 (2H, s), 7.28 (1 H, dd, J = 8.4 and 18.9Hz), 7.47 (1 H, s), 7.66-7.74 (3H, m), 7.79-7.84 (1 H, m), 7.88-7.94 (2H, m), 9.49 (1 H, s). MS (ES) m/z: 371.2 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(1H-benzo[d]imidazol-1-yl)acetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4,10-di-fmoc-deacylramoplaninamine In N,N-dimethyl-formamide at 20℃; for 8h; Stage #3: With piperidine; hydrogenchloride; water more than 3 stages; | 45 To a stirred solution of benzimidazol-1-ylacetic acid (35 mg) in DMF (0.5 mL) was added EDC (39 mg), and the resultant mixture was stirred at room temperature for 30 min. An aliquot (50 μL) of this reaction mixture was added to a solution of 4,10-diFmoc-deacylramoplanin amine (20 mg) in DMF (300 μL). This was stirred at room temperature for 8 h, the reaction mixture was diluted with water (3 mL), and then the precipitated solid was filtered off and dried under high vacuum (15 mg). This was dissolved in DMF (300 μL) and piperidine was added (15 μL), and the mixture was stirred for 12 min. The reaction mixture was diluted with acetonitrile (500 μL) followed by addition of 0.5 N hydrochloric acid (600 μL). The product was purified by preparative HPLC to obtain Example 45. HPLC: Rt=4.523 min (Condition 1); Rt=5.888 min (Condition 3). ESMS: m/z 1288.5 [(M+2H)/2]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.5% | Stage #1: 2-(1H-benzo[d]imidazol-1-yl)acetic acid With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-(4-chlorophenyl)-2-thiazolamine With pyridine In N,N-dimethyl-formamide at 20℃; for 17h; | 1.C To a solution of (1H-benzimidazol-1-yl)acetic acid (1 g, 5.68 mmol) (Example 1B) in N,N-dimethylformamide (25 mL) was added thionyl chloride (0.4 mL, 5.56 mmol) dropwise and the reaction mixture stirred at room temperature for 1 h. 2-Amino-4-(4-chlorophenyl)thiazole (1.15 g, 5.46 mmol) and pyridine (4 mL) were then added to the reaction mixture and stirred at room temperature for 17 h. The reaction mixture was then concentrated in vacuo and dichloromethane was added and transferred to a separating funnel where the organics were washed with 0.1 M hydrochloric acid and 10% ammonium hydroxide solution. The organic layers were combined and washed with saturated aqueous sodium chloride, dried (Mg2SO4), filtered and concentrated in vacuo. The residue was then purified by column chromatography using silica and eluting with 0-10% methanol in dichloromethane, affording the title compound (93.7 mg, 4.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.34 (2H, s), 7.19-7.27 (2H, m), 7.51 (1H, d, J=8.5 Hz), 7.59 (1H, d, J=7.2 Hz), 7.68 (1H, d, J=7.1 Hz), 7.71 (1H, s), 7.93 (2H, d, J=8.5 Hz), 8.25 (1H, s), 12.79 (1H, s). MS (ES) m/z: 369.0 [M+H]. |
4.5% | Stage #1: 2-(1H-benzo[d]imidazol-1-yl)acetic acid With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-(4-chlorophenyl)-2-thiazolamine With pyridine In N,N-dimethyl-formamide at 20℃; for 17h; | 1.C C: 2-benzimidazol-1-yl-N-r4-(4-chloro-phenyl)-thiazol-2-yll-acetamide. To a solution of (1 H-benzimidazol-1-yl)acetic acid (1g, 5.68mmol) (Example 1B) in λ/,λ/-dimethylformamide (25ml_) was added thionyl chloride (0.4ml_, 5.56mmol) dropwise and the reaction mixture stirred at room temperature for 1 h. 2-Amino-4-(4- chlorophenyl)thiazole (1.15g, 5.46mmol) and pyridine (4ml_) were then added to the reaction mixture and stirred at room temperature for 17h. The reaction mixture was then concentrated in vacuo and dichloromethane was added and transferred to a separating funnel where the organics were washed with 0.1 M hydrochloric acid and 10% ammonium hydroxide solution. The organic layers were combined and washed with saturated aqueous sodium chloride, dried (Mg2SO4), filtered and concentrated in vacuo. The residue was then purified by column chromatography using silica and eluting with 0- 10% methanol in dichloromethane, affording the title compound (93.7 mg, 4.5 %). 1H NMR (400MHz, DMSO-c/6) δ ppm 5.34 (2H, s), 7.19-7.27 (2H, m), 7.51 (1 H, d, J = 8.5Hz), 7.59 (1 H, d, J = 7.2Hz), 7.68 (1 H, d, J = 7.1 Hz), 7.71 (1 H, s), 7.93 (2H, d, J = 8.5Hz), 8.25 (1 H, s), 12.79 (1 H, s). MS (ES) m/z: 369.0 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | Stage #1: 2-(1H-benzo[d]imidazol-1-yl)acetic acid With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide; toluene at 20℃; for 24h; Stage #2: 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine In N,N-dimethyl-formamide; toluene at 20℃; for 24h; | 2.B (1H-Benzimidazol-1-yl)acetic acid (50 mg, 0.28 mmol) (Example 1B) was dissolved in toluene and N,N-dimethylformamide. Triethylamine (0.03 mL, 0.42 mmol) then added followed by diphenyl phosphoryl azide (DPPA) (0.07 mL, 0.36 mmol) and stirred at room temperature for 24 h. 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine (57 mg, 0.21 mmol) (Example 2A) was then added in one portion and the mixture stirred for 24 h at room temperature. Mixture was evaporated to dryness and DMSO (1 mL) added before purification by preparative LCMS to give an oily residue (8.9 mg, 7%). 1H NMR (400 MHz, CD3OD) δ ppm 3.81 (3H, s), 5.34 (2H, s), 7.29-7.36 (3H, m), 7.42 (1H, d, J=2.5 Hz), 7.53 (1H, d, J=7.2 Hz), 7.72 (1H, d, J=7.1 Hz), 8.06 (1H, d, J=2.6 Hz), 8.25 (1H, s). MS (ES) m/z: 434.3 [M+H]. |
7% | Stage #1: 2-(1H-benzo[d]imidazol-1-yl)acetic acid With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide; toluene at 20℃; for 24h; Stage #2: 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine In N,N-dimethyl-formamide; toluene at 20℃; for 24h; | 2.B B: 2-benzimidazol-1-yl-N-r4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-yll-acetamide (1 H-Benzimidazol-1-yl)acetic acid (50mg, 0.28mmol) (Example IjJ) was dissolved in toluene and λ/,λ/-dimethylformamide. Triethylamine (0.03ml_, 0.42mmol) then added followed by diphenyl phosphoryl azide (DPPA) (0.07ml_, 0.36mmol) and stirred at room temperature for 24h. 4-(3,5-dichloro-2-methoxy-phenyl)-thiazol-2-ylamine (57mg, 0.21 mmol)(Example 2A) was then added in one portion and the mixture stirred for 24h at room temperature. Mixture was evaporated to dryness and DMSO (1 mL) added before purification by preparative LCMS to give an oily residue (8.9mg, 7%). 1H NMR (400MHz, CD3OD) δ ppm 3.81 (3H, s), 5.34 (2H, s), 7.29-7.36 (3H, m), 7.42 (1 H, d, J = 2.5Hz), 7.53 (1 H, d, J = 7.2Hz), 7.72 (1 H, d, J = 7.1 Hz), 8.06 (1 H, d, J = 2.6Hz), 8.25 (1 H, s). MS (ES) m/z: 434.3 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2.2-Benzimidazol-1-yl-N-(6-phenyl-pyridin-2-yl)-acetamide; To a solution of (1 H-benzimidazol-1-yl)acetic acid (1g, 5.68mmol) (Example MZ) in lambda/,lambda/-dimethylformamide (25mL) was added thionyl chloride (0.4ml_, 5.56mmol) drop- wise and the reaction mixture stirred at room temperature for 1 h. 6-Phenyl-pyridin-2- ylamine (5.46mmol) and pyridine (4mL) were then added to the reaction mixture and stirred at room temperature for 17h. The reaction mixture was then concentrated in vacuo and dichloromethane was added and transferred to a separating funnel where the organics were washed with 0.1 M hydrochloric acid and 10% ammonium hydroxide solution. The organic layers were combined and washed with saturated aqueous sodium chloride, dried (Mg2SO4), filtered and concentrated in vacuo. The residue was then purified by column chromatography using silica and eluting with 0-10% methanol in dichloromethane, affording the title compound. 1H NMR (400MHz, CD3OD) delta ppm 5.29 (2H, s), 7.28-7.35 (2H, m), 7.39-7.48 (3H, m), 7.54 (1 H, d, J = 7.2Hz), 7.62 (1 H, d, J = 7.7Hz), 7.71 (1 H, d, J = 7.3Hz), 7.81 (1 H, t, J = 7.9Hz), 7.98 (1 H, br d), 8.05 (2H, d, J = 7.3Hz), 8.23 (1 H, s). MS (ES) m/z: 329.1 [M+H]. |
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