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[ CAS No. 69189-26-0 ] {[proInfo.proName]}

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Chemical Structure| 69189-26-0
Chemical Structure| 69189-26-0
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Product Details of [ 69189-26-0 ]

CAS No. :69189-26-0 MDL No. :MFCD13178503
Formula : C9H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 162.19 Pubchem ID :-
Synonyms :

Safety of [ 69189-26-0 ]

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:

Application In Synthesis of [ 69189-26-0 ]

* 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.

  • Downstream synthetic route of [ 69189-26-0 ]

[ 69189-26-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 564467-91-0 ]
  • [ 69189-26-0 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen; In methanol; ethanol; at 20℃; under 760.051 Torr; for 18.0h;Inert atmosphere; Pd/C (10%, 96.911 mg, 0.0911 mmol) was added to a stirred solution of 1-34 (700 mg, 3.64 mmol) in MeOH (8 mL) and EtOH (8 mL) under nitrogen atmosphere. The mixture was hydrogenated H2 (atmospheric pressure) at rt for 18h. The mixture was filtered through a pad of diatomaceous earth and the residue was washed with MeOH. The filtrate was evaporated in vacuo to yield 1-35 (590.78 mg, quantitative) as a yellow solid.
86% With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 3.0h; To a solution of 2-methyl-6-nitroisoindolin-1-one (62.4) (146 mg, 0.76 mmol) in methanol (14 mL) was added 15mg Pd/C. The reaction mixture was stirred at ambient temperature for 3 h under H2. TLC showed the reaction was complete. The reaction mixture was filtered, and the filtrate was concentrated to afford 6-amino-2-methylisoindolin-1-one (62.5) as a yellow solid (106 mg, 86%). [00893] 1HNMR (400 MHz, CDCl3): δ 3.16 (s, 3H), 3.82 (br, 2H), 4.25 (s, 2H), 6.83 (dd, 1H), 7.11 (d, 1H), 7.18 (d, 1H)
  • 2
  • [ 5342-91-6 ]
  • [ 69189-26-0 ]
  • 3
  • [ 69189-26-0 ]
  • (R)-1-(3-((2-chloro-5-fluoropyrimidin-4-yl)amino)piperidin-1-yl)prop-2-en-1-one [ No CAS ]
  • (R)-6-((4-((1-acryloylpiperidin-3-yl)amino)-5-fluoropyrimidin-2-yl)amino)-2-methylisoindolin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; DavePhos; In tert-Amyl alcohol; at 100℃; for 3.0h;Inert atmosphere; To a solution of <strong>[69189-26-0]6-amino-2-methylisoindolin-1-one</strong> (62.5) (106 mg, 0.65 mmol) in tert-amyl alcohol (15 mL) was added (R)-1-(3-((2-chloro-5-fluoropyrimidin-4- yl)amino)piperidin-1-yl)prop-2-en-1-one (intermediate B, 186 mg, 0.62 mmol), Davephos (51 mg, 0.13 mmol), tris(dibenzylideneacetone)dipalladium(0) (59 mg, 0.07 mmol), and Cs2CO3 (426 mg, 1.31 mmol). The reaction mixture was stirred at 100 C for 3 h under N2. TLC showed the reaction was complete. The reaction mixture was quenched with the addition of water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to afford the crude product. The crude product was purified by column chromatography (DCM/MeOH: 20/1) to afford ((R)-6-((4-((1- acryloylpiperidin-3-yl)amino)-5-fluoropyrimidin-2-yl)amino)-2-methylisoindolin-1-one (I-62) as a yellow solid (140 mg, 52%). [00896] LCMS: 411.4 [M+1]+. [00897] 1HNMR (400 MHz, DMSO-d6): δ 1.49-1.63 (m, 2H), 1.80 (d, 1H), 1.98-2.03 (m, 1H), 2.77-2.88 (m, 1H), 3.04 (s, 3.5H), 3.18-3.24 (m, 0.5H), 3.94-4.13 (m, 2.5H), 4.34 (d, 2.5H), 5.47 (d, 0.5H), 5.68 (d, 0.5H), 6.04 (dd, 1H), 6.58-6.64 (m, 0.5H), 6.79-6.86 (m, 0.5H), 7.37 (t, 2H), 7.78-7.82 (m, 1H), 7.95 (d, 1H), 8.13 (s, 1H), 9.30 (s, 1H).
  • 4
  • [ 1975-52-6 ]
  • [ 69189-26-0 ]
  • 5
  • [ 77324-87-9 ]
  • [ 69189-26-0 ]
  • 6
  • [ 90725-68-1 ]
  • [ 69189-26-0 ]
  • 7
  • [ 69189-26-0 ]
  • [ 62595-74-8 ]
  • C14H15N3O3 [ No CAS ]
  • 8
  • [ 69189-26-0 ]
  • C9H8Br2N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With bromine; acetic acid; In chloroform; at 20℃; for 16.0h; 1-35 (0.591 g, 3.643 mmol) was dissolved in acetic acid (7.5 mL) and CHCL (7.5 mL). Then a solution of Br2 (0.411 mL, 8.01 mmol) in acetic acid (2.5 mL) and CHCL (2.5 mL) was added under vigorous stirring. The mixture was stirred at rt for 16 h. DCM was added and the solution was washed with water and sat NaHC03 . The organic phase was dried over MgS04., filtered, and volatiles were evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; EtOAc in heptane, gradient from 0/100 to 100/0). The desired fractions were collected and concentrated in vacuo to yield 1-36 (373 mg, 32%) as a yellow solid.
  • 9
  • [ 69189-26-0 ]
  • C11H14N2O [ No CAS ]
  • 10
  • [ 69189-26-0 ]
  • [ 955369-56-9 ]
  • 2-allyl-1-(6-(2-hydroxypropane-2-yl)pyridin-2-yl)-6-((2-methyl-3-oxoisoindolin-5-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.6mg To a toluene solution (5 mL) of compound Int-1 (100 mg), m-CPBA (146 mg) was added and stirred at room temperature overnight to obtain a solution A. NaH (56 mg) was added to a DMF (5 mL) solution in which Compound A-31 (59 mg) was dissolved, and stirred at room temperature for 30 minutes to obtain a mixture B. Then A was slowly added to B and stirred overnight at room temperature. The reaction solution was poured into a saturated ammonium chloride solution, a white solid was precipitated, and the filter cake was purified by thin layer chromatography TLC (dichloromethane: methanol (v / v) = 20: 1) to obtain the standard product HY-B031 (2.6 mg) as a white solid.
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