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Chemical Structure| 1062246-03-0 Chemical Structure| 1062246-03-0

Structure of 1062246-03-0

Chemical Structure| 1062246-03-0

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Product Details of [ 1062246-03-0 ]

CAS No. :1062246-03-0
Formula : C13H15ClF2N4O
M.W : 316.73
SMILES Code : O=C1N(C)C2=CN=C(Cl)N=C2N(C3CCCC3)CC1(F)F
MDL No. :MFCD25542098

Safety of [ 1062246-03-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 1062246-03-0 ]

* 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 [ 1062246-03-0 ]

[ 1062246-03-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1001345-78-3 ]
  • [ 1062246-03-0 ]
  • [ 1137868-52-0 ]
YieldReaction ConditionsOperation in experiment
4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H- pyrimido[4,5-b][l,4]diazepin-2-ylamino)-2-fluoro-5-methoxy-N-(l-methylpiperidin-4- yl)benzamide: A mixture of 2-chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro- 5H-pyrimido[4,5-b][l,4]diazepin-6(7H)-one (25 g, 79.1 mmol), 4-amino-2-fluoro-5- methoxy-N-(l-methylpiperidin-4-yl)benzamide (23.3 g, 83 mmol), isopropanol (197 ml), and concentrated hydrochloric acid (8 mL) was stirred in an oil bath of 1000C (temp, inside the flask was 83 0C) for 3 days (lots of precipitate appeared after first day of stirring). The reaction mixture was cooled down and the white solid was filtered and washed with more iPrOH, finally dired to give 40 g tan solid as HCl salt. Above obtained HCl salt (40 g) was dissolved in 1 L of MeOH with an effective stirring bar. It was cooled to 0 0C, sodium bicarbonate solid (28.1 g, 0.33 mol) was added slowly. <n="416"/>The reaction mixture was then stirred at r.t for 4 h. After which, it was filtered through a pad of celite. The filtrate concentrated in vacuo to 500 mL in volume, and 500 mL of water was charged into the flask. The mixture was then kept on rotavaping at 20 0C. Lots of pinkish precipitate appeared. Until around 100 mL of MeOH left, 500 mL more of water was added to the flask. The whole was filtered, solid washed with more water (500 mL) and dried to give 35 g of product as light pinkish solid (>99 percent pure by LC). To a 500 mL round bottom flask, was added 60 g of the free base and EtOH (200 ml). It was heated at 85 0C for 0.5 h. It was then cooled down, solid filtered and washed with more EtOH (200 mL). When dried, around 48 g of off- white solid was obtained (filtrate contained color and some impurities). The solid was then completely dissolved in 4L of MeOH, filtered on the paper. The filtrate was concentrated to a solid. It was then dissolved in 200 mL of EtOH. The suspension was then heated at 60 0C with effective stirring for 24 h. The slurry was then cooled down gradually to room temperature, filtered. The solid was washed with more EtOH (200 mL), dried in a vacuum oven (60 0C) for 3 days. Finally, 44 g of product as white solid was obtained (73percent recovery). The combined filtrate (contained mostly product) was concentrated and set aside for further purification by prep-HPLC. 1H NMR (400 MHz, DMSO-J6) delta ppm 1.47 - 1.82 (m, 10 H) 1.90 - 2.04 (m, 4 H) 2.16 (s, 3 H) 2.74 (d, J= 11.6 Hz, 2 H) 3.63 - 3.77 (m, 1 H) 3.92 (s, 3 H) 4.09 (t, J= 13.9 Hz, 2 H) 4.82 (m, 1 H) 7.19 (d, J= 6.8 Hz, 1 H) 7.91 (dd, J= 7.7, 3.4 Hz, 1 H) 8.04 (d, J= 1.3 Hz, 1 H) 8.25 (d, J= 13.4 Hz, 1 H) 8.31 (s, 1 H). Melting point 194.5-195.5 0C. [M+H] calc'd for C27H34F3N7O3, 562; found 562.
  • 2
  • [ 1062246-03-0 ]
  • [ 1137868-52-0 ]
 

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