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[ CAS No. 957054-30-7 ] {[proInfo.proName]}

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Chemical Structure| 957054-30-7
Chemical Structure| 957054-30-7
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Product Details of [ 957054-30-7 ]

CAS No. :957054-30-7 MDL No. :MFCD11616196
Formula : C23H27N7O3S2 Boiling Point : -
Linear Structure Formula :- InChI Key :LHNIIDJUOCFXAP-UHFFFAOYSA-N
M.W : 513.64 Pubchem ID :17755052
Synonyms :
GDC-0941;GNE-0941;Pictrelisib;RG7321

Safety of [ 957054-30-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 957054-30-7 ]

* 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.

  • Upstream synthesis route of [ 957054-30-7 ]
  • Downstream synthetic route of [ 957054-30-7 ]

[ 957054-30-7 ] Synthesis Path-Upstream   1~13

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YieldReaction ConditionsOperation in experiment
37% With sodium hydrogencarbonate In ethanol; water; toluene at 120℃; for 1 h; Inert atmosphere; Microwave irradiation Step li: 4-(2-Chloro-6-((4-(methylthioperoxy)piperazin-l-yl)methyl)thieno[3,2-d] pyrimidin-4-yl)morpholine (Compound 0114)A mixture of compound 0113 (800 mg, 1.86 mmol), 0107-3 (500 mg, 2.04 mmol), sodium hydrogen carbonate (470 mg, 5.58 mmol) and bis(triphenylphosphine) palladium(O) chloride (80 mg, 0.093 mmol) in toluene (20 mL), ethanol (12 mL) and water (5.6 mL) was flushed with nitrogen and heated under microwave irradiation at 120 °C for 1 h. The reaction mixture was partitioned between dichloromethane and water. The organic layer was separated and washed with brine, dried over magnesium sulfate, filtered and evaporated. The resulting residue was purified by column chromatography (silica gel, dichloromethane, 2percent, v/v, to give title compound 0114 (350 mg, 37percent) as a white solid, mp 148-149 °C. LCMS: 514 [M+l]+; 1H NMR (400 MHz, CDC13): δ 2.70 (t, J= 4.4 Hz, 4H), 2.81(s, 3H), 3.13 (t, J= 4.4 Hz , 4H), 3.92 (m, 6H), 4.09 (t, J= 5.6 Hz, 4H), 7.41 (s, 1H), 7.50 (m, 1H), 7.59 (d, J= 8.4 Hz , 1H), 8.28 (d, J= 6.8 Hz , 1H), 9.00 (s, 1H), 10.32 (br s, 1H).
37% With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In water; toluene at 120℃; for 1 h; Inert atmosphere; Microwave irradiation Step 1i: 4-(2-Chloro-6-((4-(methylthioperoxy)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine (Compound 0114)[0179]A mixture of compound 0113 (800 mg, 1.86 mmol), 0107-3 (500 mg, 2.04 mmol), sodium hydrogen carbonate (470 mg, 5.58 mmol) and bis(triphenylphosphine) palladium(0) chloride (80 mg, 0.093 mmol) in toluene (20 mL), ethanol (12 mL) and water (5.6 mL) was flushed with nitrogen and heated under microwave irradiation at 120° C. for 1 h. The reaction mixture was partitioned between dichloromethane and water. The organic layer was separated and washed with brine, dried over magnesium sulfate, filtered and evaporated. The resulting residue was purified by column chromatography (silica gel, dichloromethane, 2percent, v/v), to give title compound 0114 (350 mg, 37percent) as a white solid. mp 148-149° C. LCMS: 514 [M+1]+; 1H NMR (400 MHz, CDCl3): δ 2.70 (t, J=4.4 Hz, 4H), 2.81 (s, 3H), 3.13 (t, J=4.4 Hz, 4H), 3.92 (m, 6H), 4.09 (t, J=5.6 Hz, 4H), 7.41 (s, 1H), 7.50 (m, 1H), 7.59 (d, J=8.4 Hz, 1H), 8.28 (d, J=6.8 Hz, 1H), 9.00 (s, 1H), 10.32 (br s, 1H).
37% With sodium hydrogencarbonate In ethanol; water; toluene at 120℃; for 1 h; Inert atmosphere; Microwave irradiation In toluene (20 mL), ethanol (12 mL) and water (5.6 mL), compound 0113 (800mg, 1.86mmol), 0107-3 (500mg, 2.04mmol), sodium bicarbonate (470 mg, 5.58 mmol) and bis (tri sprayed with nitrogen to a mixture of triphenylphosphine) palladium (O) (80mg, 0.093mmol), it was heated under microwave irradiation for 1 hour at 120. ° C.. The reaction mixture was partitioned between dichloromethane and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and evaporated. The resulting residue was purified by column chromatography (silica gel, dichloromethane, to give 2percent, v / v, the title compound 0114 a (350 mg, 37percent) as a white solid.
1.4 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; water; toluene at 130℃; for 1.5 h; Microwave irradiation A mixture of 4-(2-chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine 31 from Example 4 (2.00 g), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole 7 (2.26 g), toluene (24 mL), ethanol (12 mL), water (6 mL), sodium carbonate (1.72 g) and PdCl2(PPh3)2 (325 mg) was heated to 130° C. in the microwave for 90 minutes (US 2008/0076768; WO 2006/046031, incorporated by reference herein).
The reaction mixture was cooled, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent removed in vacuo.
The residue was purified using flash chromatography (ethyl acetate then 5percent ethyl acetate/methanol) and then trituration with ether yielded Formula Ia compound, GDC-0941 (1.4 g). MS data: (ESI+): MH+ 514. NMR data: (CDCl3): 2.67-2.71 (4H, m), 2.81 (3H, s), 3.29-3.33 (4H, m), 3.89 (2H, s), 3.89-3.93 (4H, m), 4.08-4.12 (4H, m), 7.41 (1H, s), 7.51 (1H, t, J=7.2), 7.60 (1H, d, J=8.3), 8.28 (1H, d, J=7.5), 9.02 (1H, s), 10.10 (1H, br)
1.4 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; water; toluene at 130℃; for 1.5 h; Inert atmosphere; Microwave irradiation A mixture of 4-(2-chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine 31 from Example 4 (2.00 g), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole 7 (2.26 g), toluene (24 mL), ethanol (12 mL), water(6 mL), sodium carbonate (1.72 g) and PdCl2(PPh3)2(325 mg) was heated to 130° C. in the microwave for 90 minutes (US 2008/0076768; WO 2006/046031, incorporated by reference herein).The reaction mixture was cooled, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography (ethyl acetate then 5percent ethyl acetate/methanol) and then trituration with ether yielded Formula Ia compound, GDC-0941 (1.4 g).

Reference: [1] Patent: WO2011/130628, 2011, A1, . Location in patent: Page/Page column 130
[2] Patent: US2013/102595, 2013, A1, . Location in patent: Paragraph 0179
[3] Patent: JP2015/187145, 2015, A, . Location in patent: Paragraph 0177
[4] Patent: US2008/76768, 2008, A1, . Location in patent: Page/Page column 9-10
[5] Patent: US9335320, 2016, B2, . Location in patent: Page/Page column 76
[6] Patent: JP5658565, 2015, B2, . Location in patent: Paragraph 0361-0363
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Reference: [1] Patent: US2010/233164, 2010, A1,
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Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: US9335320, 2016, B2,
[3] Patent: JP2015/187145, 2015, A,
[4] Patent: JP5658565, 2015, B2,
[5] Patent: US2013/102595, 2013, A1,
  • 4
  • [ 22288-78-4 ]
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Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: US9335320, 2016, B2,
[3] Patent: JP2015/187145, 2015, A,
[4] Patent: JP5658565, 2015, B2,
[5] Patent: US2013/102595, 2013, A1,
  • 5
  • [ 16234-14-3 ]
  • [ 957054-30-7 ]
Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: US9335320, 2016, B2,
[3] Patent: JP2015/187145, 2015, A,
[4] Patent: JP5658565, 2015, B2,
[5] Patent: US2013/102595, 2013, A1,
  • 6
  • [ 16234-15-4 ]
  • [ 957054-30-7 ]
Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: US9335320, 2016, B2,
[3] Patent: JP2015/187145, 2015, A,
[4] Patent: JP5658565, 2015, B2,
[5] Patent: US2013/102595, 2013, A1,
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Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: WO2011/130628, 2011, A1,
[3] Patent: JP2015/187145, 2015, A,
[4] Patent: JP2015/187145, 2015, A,
[5] Patent: US2013/102595, 2013, A1,
[6] Patent: US2013/102595, 2013, A1,
  • 8
  • [ 885618-31-5 ]
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Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: US9335320, 2016, B2,
[3] Patent: JP2015/187145, 2015, A,
[4] Patent: US2013/102595, 2013, A1,
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Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 18, p. 5522 - 5532
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Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: JP2015/187145, 2015, A,
[3] Patent: US2013/102595, 2013, A1,
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Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: JP2015/187145, 2015, A,
[3] Patent: US2013/102595, 2013, A1,
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Reference: [1] Patent: JP2015/187145, 2015, A,
[2] Patent: JP5658565, 2015, B2,
[3] Patent: US2013/102595, 2013, A1,
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Reference: [1] Patent: JP5658565, 2015, B2,
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