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Structure of 20028-40-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 20028-40-4 |
Formula : | C9H11N3 |
M.W : | 161.20 |
SMILES Code : | CN1C(CN)=NC2=C1C=CC=C2 |
MDL No. : | MFCD00457746 |
InChI Key : | GFQZSGGPNZDNBC-UHFFFAOYSA-N |
Pubchem ID : | 800907 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3259 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
Step 1b 1-Methyl-2-(aminomethyl)benzimidazole Add the product (Preparation 12, Step 1a) (10.3 g) to a solution of potassium hydroxide (5.20 g) in methanol (200 mL). Stir the resulting mixture at room temperature for 30 minutes, filter, and concentrate the filtrate in vacuo. Extract the with EtOAc (400 mL) and filter. Concentrate the filtrate in vacuo to give the title compound as a white solid (5.60 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; at 20℃; for 0.5h; | Step 1b; 1-Methyl-2-(aminomethyl)benzimidazole; [Show Image] Add the product (Preparation 12, Step 1a) (10.3 g) to a solution of potassium hydroxide (5.20 g) in methanol (200 mL). Stir the resulting mixture at room temperature for 30 minutes, filter, and concentrate the filtrate in vacuo. Extract the with EtOAc (400 mL) and filter. Concentrate the filtrate in vacuo to give the title compound as a white solid (5.60 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; for 18h; | Step 2; N3-[4-[(1-Methylbenzimidazol-2-yl)methyl]aminomethylbenzoyl)-N2-Cbz-L-2,3-diaminopropionic acid on 2-chlorotrityl resin; [Show Image] Shake the resin (Preparation 4, Step 1) (1.50 g, 0.60 mmol) and <strong>[20028-40-4]1-methyl-2-(aminomethyl)benzimidazole</strong> (5.00 g) in DMF (25 mL) in a sealed vial for 18 hours. Transfer resin to funnel apparatus, and wash the resin with DMF (25 mL x 5) and then CH2Cl2 (20 mL x 5) to give the title resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | 7.9 grams (11.04 mmol, 1.9 eq) of PL-TFP Resin (source: Polymer Laboratories) was weighed into a pressure tube. 60 ml of DCM was added. 2 g (5.74 mmol) of 3-(4-(3- acetamidophenyl)pyrimidin-2-ylamino)benzoic acid was dissolved in 15 ml of DMF and[0 After 10 min, this solution was added to the pressure tube. Dimethylaminopyridine (4.41 mmol, .6 eq, source: Acros) was added to the pressure tube as a solid, followed by 1,3- diisopropylcarbodiimide (33.08 mmol, 4.5 eq, source: Acros). The pressure tube was sealed and the reaction was placed on a vertical shaker overnight. The resin was filtered, and then washed 3 times with DMF, followed by three times with THF, followed by three times with.5 DCM. The resin was then dried overnight by vaccum.[0270] 300 mg of resin prepared above (loading = 0.6 mmol/g, .18 mmol) was added to a 1 dram vial. 2 ml of DMA were added. 1 ml of (1 -methyl- lH-benzo[d] imidazol-2- yl)methanamine (0.12 mmol, 0.67 eq) dissolved in DMA was added to the vial. The reaction was stirred overnight at room temperature. The reaction was filtered and rinsed twice with 410 ml of MeOH. The solution was further purified by HPLC to yield ( 3-(4-(4- acetamidophenyl)pyrimidin-2-ylamino)-N-(( 1 -methyl- 1 H-benzo[d]imidazol-2- yl)methyl)benzamide 83 (10.2 mg, 17%). <n="275"/>1H-NMR (400MHz, d6-DMSO): 10.23 (s, IH), 9.80 (s, IH), 9.01 (t, IH), 8.52 (t, 2H), 8.17- 8.19 (m, 2H), 7.91-7.93 (m, IH), 7.75 (d, 2H), 7.50-7.59 (m, 3H), 7.39-7.43 (m, 2H), 7.16- 7.26 (m, 2H), 4.80 (d, 2H), 3.86 (s, 3H), 2.10 (s, 3H). MS (EI) for C28H25N7O2: 492.4 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 41 2-[1-(3,4-Dimethoxy-benzyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-N-(1-methyl-1H-benzoimidazol-2-ylmethyl)-2-phenyl-acetamide: prepared by reaction of [1-(3,4-dimethoxy-benzyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-phenyl-acetic acid with <strong>[20028-40-4]C-(1-methyl-1H-benzoimidazol-2-yl)-methylamine</strong>. LC-MS: rt=3.50 min, 635 (M+1, ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In methanol; at 20℃; for 5h; | <strong>[20028-40-4](1-methyl-1H-benzo[d]imidazol-2-yl)methanamine</strong> (0.97 g, 6 mmol) was dissolved in dry CH3OH(10 mmL), and Cp3 (1.31 g, 5 mmol) was added, then, the mixture was stirred at room temperature for 5 h. Afterwards, the yellow precipitate was collected by filtration and purified by silica gel column chromatography (CH2Cl2:CH3OH= 20:1) to yield the desired product Cp2 as a yellow powder (1.46 g, 72% yield). IR (KBr, cm-1): 3442,3045, 2925, 1749, 1640, 1581, 1509, 1428, 1381, 1351, 1301, 1241, 825, 793, 737; MS (ESI-TOF): m/z = 406.1389 (M+); M+ calculated 406.1403; 1H NMR (400MHz, DMSO-d6) delta(ppm): 1.27-1.31 (t, 3H, J = 8Hz CH3) 3.83 (s, 3H, CH3), 4.22-4.28 (q, 2H, J = 8Hz, CH2), 5.38 (s, 2H, CH2), 6.50-6.53 (d, 1H, J = 12Hz, ArH), 7.19-7.25 (m, 2H, ArH), 7.57-7.62 (m, 2H, ArH), 7.69-7.71 (d, 1H, J = 8Hz, ArH), 8.60 (s, 1H, =CH), 9.13-9.16 (d, 1H, J = 12Hz, =CH), 14.20 (s, 1H, OH); 13CNMR (100MHz, DMSO-d6) delta(ppm): 179.38, 163.15, 161.77, 160.34, 155.89, 150.08, 149.93, 141.86, 135.96, 135.78, 122.36, 121.75, 121.28, 118.85, 110.21, 107.14, 104.71, 103.31, 60.53, 47.16, 29.71, 14.26. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 110℃;Sealed tube; | Example 4106-(2 , 3-Dimethylphenyl)-4-N-[2-(4-methanesulfonylphenyl)ethyl]pyrim idine-2 4-diamine.A mixture of 4-chloro-6-(2,3-dimethylphenyl)pyrimidin-2-amine (0.14 mmol), <strong>[20028-40-4](1-methylbenzimidazol-2-yl)methanamine</strong> (1.2 eq.) and N, N-diisopropylethylamine(1.25 eq.) in n-butanol (0.3 mL) was heated in a sealed tube at 11000 overnight.Methanol was added and the mixture was filtered and purified by preparativeH PLC. LCMS [M+H] 359. | |
With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 110℃;Sealed tube; | Example 410 6-(2,3-Dimethylphenyl)-4-N-[2-(4-methanesulfonylphenyl)ethyl]pyrimidine-2,4- diamine. A mixture of 4-chloro-6-(2,3-dimethylphenyl)pyrimidin-2-amine (0.14 mmol), (1- methylbenzimidazol-2-yl)methanamine (1.2 equiv.) and N,N- diisopropylethylamine (1.25 equiv.) in n-butanol (0.3 mL) was heated in a sealed tube at 1 10C overnight. Methanol was added and the mixture was filtered and purified by preparative HPLC. LCMS [M+H]+ 359. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With trifluoroacetic acid; In dichloromethane; at 20℃; for 2h; | A mixture of tert-butyl ((i-methyl-i H-benzo [d] imidazol-2-yl)methyl)carbamate (2.53 g, 9.68 mmol) in TFA (20 mL) and DCM (80 mL) was stirred at RT for 2 h. The solution was appliedto an SCX-2 cartridge (75 g, prewashed with DCM). The cartridge was washed with MeOH then the product eluted with 2M NH3 in MeOH; concentration in vacuo left a brown solid (1.63 g, quant.). M/z 162 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iron(III) chloride hexahydrate; In isopropyl alcohol; at 140℃; for 0.25h;Sealed tube; Microwave irradiation; | 1.0 mmol of <strong>[20028-40-4]N-methylbenzimidazole methylamine</strong> (161.0 mg)Adding to a reaction vessel with a volume of 100.0 mL of Teflon,After adding 40.0 mL of isopropanol to dissolve,Add 0.2 mmol of ferric chloride hexahydrate (54.0 mg),Stir for 5 minutes, seal, and put in a microwave digestion apparatus at 140 C for 10 min.The mother liquor is then spin-dried, sampled, and subjected to column chromatography.The product diffuses through the interface to obtain a pale yellow single crystal, which belongs to the monoclinic system. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With iron(III) chloride hexahydrate; In methanol; at 140℃; for 1h;Microwave irradiation; | 1.00 mmol of <strong>[20028-40-4]N-methylbenzimidazole methylamine</strong> (162 mg) was added to a reactor of 100 mL capacity of polytetrafluoroethylene, and dissolved in 40 mL of methanol.Add 0.3 mmol of anhydrous ferric chloride (54 mg), stir for 5 minutes, seal, and put in a microwave digestion apparatus at 140 C for 1 h.Then, it was naturally cooled to obtain a blue solution, which was then evaporated in an air atmosphere to obtain a purple-red crystal (32 mg, yield: 20%). Further, the obtained purple-red crystals are reacted with potassium carbonate or potassium hydroxide aqueous solution to remove HCl molecules, and separated by filtration to obtain neutral radical molecules. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To asolution of 1 g (2.7 mmol) of 10 in 20 ml of DCM was added 1.2 ml(8.1 mmol) of TEA. This solution stirred at room temperature for15 min followed by the addition of TBTU (0.82 g, 3.3 mmol). Theresulting mixture stirred for 15 min, and 3.3 mmol of the corresponding(heterocyclylmethyl)amine 7 was added. The reactionmixture was washed with a 10% aqueous solution of potash andwater. The organic layer was dried over sodium sulfate and evaporatedon a rotary evaporator. Diethyl ether was added to the residue,and the resulting precipitatewas filtered and dried in vacuo. Atotal of 1.8 mmol of 8 was dissolved in a mixture of 18 ml of THF and2 ml of methanol, 0.09 g of 10% Pd/C was added, and the mixturestirred under a hydrogen atmosphere for 8 h. The reaction mixturewas passed through Celite and the filtrate was evaporated. Theresidue was stirred with ether, filtered and dried in vacuo. |
A965446 [53332-79-9]
[(1-Methyl-1H-benzimidazol-2-yl)methyl]amine dihydrochloride
Reason: Free-salt