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Structure of 41995-29-3
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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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CAS No. : | 41995-29-3 |
Formula : | C8H12N2 |
M.W : | 136.19 |
SMILES Code : | NC1=NC(CCC)=CC=C1 |
MDL No. : | MFCD00130076 |
InChI Key : | JDRTXRTVJTWITJ-UHFFFAOYSA-N |
Pubchem ID : | 3016309 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H315-H318-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Class: | 8 |
UN#: | 2735 |
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 |
---|---|---|
EXAMPLE 117 3-[4-(3,5-Dichloropyrid-4-ylcarboxamido)phenyl]-2-(6-propylpyrid-2-ylamino)propanoic acid A mixture of Intermediate 25 (150 mg), dirhodiumtetraacetate, (1.8 mg, 5.1 μmols) and 2-amino-6-propylpyridine in anhydrous toluene (2.5 ML) was agitated at ambient temperature for 0.5 h then at 80 C. for 6 h.. The resin was filtered and then washed with DCM, DMF, methanol, water, methanol, DMF and DCM. The resin was treated with 50% trifluoroacetic acid in DCM (4.0 ml) for 3 h with agitation and filtered. The resin was then washed with a 4.0 ml portion of DCM. The combined filtrate was evaporated in vacuo to give the crude product (48 mg) which was purified by preparative HPLC to afford the title compound (2.7 mg). HPLC-MS Retention time 2.19 min; MH+473. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; for 15h;Heating / reflux; | Example 25 Piperidine-1-sulfonic acid (6-propyl-pyridin-2-yl)-amide A solution of 6-propyl-pyridin-2-ylamine (0.2 g) and piperidine-1-sulfonyl chloride (0.296 g, Bull. Soc. Chim. Fr.; 1936, 2143) in pyridine (7 mL) was heated to reflux for 15 h. After concentration of the reaction mixture in vacuo the residue was taken up in EtOAc, which was then washed with 1N aqueous HCl, saturated brine, dried over sodium sulphate and concentrated in vacuo. The residue was applied to a silica gel column with EtOAc/toluene (9:1 to 1:1) as eluent. Combination of the purified fractions and concentration in vacuo gave the desired piperidine-1-sulfonic acid (6-propyl-pyridin-2-yl)-amide (0.133 g) as a colorless amorphous solid. MS (ESI-): 282.0 ([M-H]-). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In dichloromethane; at 20℃; for 1h; | General Procedure: Compound 7a was prepared from 3-cyano-5-fluorobenzoic acid (900 mg, 5.45 mmol), stirred at reflux in SOCl2 (15 mL) for 2 h, followed by removal of excess thionyl chloride. The residue was taken up in CH2Cl2 (2 mL) and added to a solution of 6-methylpyridin-2-amine (6a, 638 mg, 5.9 mmol) in CH2Cl2 (9 mL), DMF (2 drops) followed by addition of TEA (1.65 mL) at 0 OC. The reaction mixture was stirred at r. t. overnight and then diluted with H2O (15 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3 X 15 mL). The combined organic layer was dried with Na2SO4, and concentrated. The residue was purified by flash column chromatography (Hexane/ EtOAc/TEA 2:1: 0.03) to give a yellow foam (1.39 g, 100%); The HCl salt was made by dissolving the free base in HCl ether solution and then recrystallizing from hot MeOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | In acetonitrile; at 130℃; for 24h; | Step 1 Ethyl 6-chloro-4-(6-propylpyridin-2-ylamino)pyridazine-3-carboxylate A mixture of ethyl 4,6-dichloropyridazine-3-carboxylate (0.80 g, 3.62 mmol) and <strong>[41995-29-3]6-propylpyridin-2-amine</strong> (739 mg, 5.43 mmol) was dissolved in acetonitrile (4 mL) and heated at 130 C. After 24 h, the reaction mixture was cooled and concentrated in vacuo, then purified by chromatography (silica, 80 g, 0 to 3% acetone in dichloromethane over 15 min, then 3 to 10% acetone in dichloromethane over another 15 min) to give ethyl 6-chloro-4-(6-propylpyridin-2-ylamino)pyridazine-3-carboxylate (335 mg, 1.04 mmol, 29%) as a pale yellow crystalline solid after drying under high vacuum at room temperature. LC-MS 321.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; In ethanol; water; | A solution of 2-(2,5-dimethyl-lH-pyrrol-l-yl)-6-propylpyridine (235 mg, 1.1 mmol, leq.) in a mixture of ethanol /water : 3/1 (4.2 mL) and hydroxylamine hydrochloride (385.2 mg, 5.5 mmol, 5 eq.) was heated a l00C for about 16 hours, cooled to room temperature and extracted with ethyle acetate. The organic layer was dried over Na2S04, filtered and evaporated in vacuo. The crude product was purified by chromatography on silica gel using a gradient of 50% to 75% ethyl acetate in heptane to afford 6- propylpyridine-2 amine as a solid.H-NMR (400 MHz, CDCI3): d 7.33 (t, J= 7.7 Hz, 1H), 6.49 (d, J= 7.4 Hz, 1H), 6.31 (d, J= 7.7 Hz, 1H), 4.50 (bs, 2H), 2.57 (t, J= 7.5 Hz, 2H), 1.69 (sext, J= 7.5 Hz, 2H), 0.95 (t, J= 7.5 Hz, 3H).13C-NMR (101 MHz, CDCb): d 160.9, 158.3, 138.3, 112.6, 106.0, 40.2, 23.1, 14.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With N-Bromosuccinimide; In methanol; for 1h;Cooling with ice; | To a solution of 6 propylpyridine-2 amine (100 mg, 0.73 mmol, 1 eq.) in methanol (2.5 mL) and cooled by an ice bath was added NBS (137 mg, 1.05 eq.). The resulting mixture was stirred for 1 hour and then concentrated. Purification by flash chromatography (EtOAc/ heptane: 1/4) afforded the title compound (74 mg, 47%)1H-NMR (400 MHz, CDCI3): d 7.45 (d, J= 8.5 Hz, 1H), 6.20 (d, J= 8.5 Hz, 1H), 4.41 (bs, 2H), 2.71 (t, J= 7.8 Hz, 2H), 1.67 (sext, J= 7.7 Hz, 2H), 0.96 (t, J= 7.4 Hz, 3H).13C-NMR (101 MHz, CDCb): d 158.8, 157.0, 141.7, 108.7, 107.8, 39.5, 22.2, 14.2. |
A401966 [153140-17-1]
3-(6-Aminopyridin-2-yl)propanenitrile
Similarity: 0.92
A401966 [153140-17-1]
3-(6-Aminopyridin-2-yl)propanenitrile
Similarity: 0.92