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[ CAS No. 1053656-57-7 ]

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2D
Chemical Structure| 1053656-57-7
Chemical Structure| 1053656-57-7
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Product Details of [ 1053656-57-7 ]

CAS No. :1053656-57-7MDL No. :MFCD11109465
Formula : C12H16ClN3O2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :269.73Pubchem ID :52987620
Synonyms :

Computed Properties of [ 1053656-57-7 ]

TPSA : 55.3 H-Bond Acceptor Count : 4
XLogP3 : 1.9 H-Bond Donor Count : 0
SP3 : 0.58 Rotatable Bond Count : 2

Safety of [ 1053656-57-7 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1053656-57-7 ]

  • Upstream synthesis route of [ 1053656-57-7 ]
  • Downstream synthetic route of [ 1053656-57-7 ]

[ 1053656-57-7 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
88% With tetrachloromethane; triphenylphosphine In 1,2-dichloro-ethane at 70℃; for 2.5 h; Inert atmosphere tert-Butyl 4-chloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate
To a solution of the product of Intermediate 1, step a (1.26 g, 5.02 mmol) in DCE (36 mL) was added PPh3 (2.69 g, 10.05 mmol) followed by CCl4 (1.46 mL, 15.07 mmol) and the mixture was heated to 70° C. for 2.5 h.
The mixture was concentrated in vacuo and chromatographed on SiO2 eluting with EtOAc/Hex to afford the desired compound as a pale yellow solid (1.20 g, 88percent). MS (ESI) mass calcd. C12H16ClN3O2, 269.09. m/z found 270.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.79 (s, 1H), 4.65 (br s, 2H), 3.80-3.68 (m, 2H), 2.93-2.82 (m, 2H), 1.49 (s, 9H).
87%
Stage #1: With triphenylphosphine In 1,2-dichloro-ethane
Stage #2: With tetrachloromethane In 1,2-dichloro-ethane at 70℃; for 2.5 h;
STEP C: A mixture of 4-hydroxy-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7- carboxylic acid ter/-butyl ester ( 1 .4 g, 5.6 mmol) and triphenylphosphine (2.9 g, 1 1.1 mmol) was stirred in DCE (41 mL) until the solution became clear, and then carbon tetrachloride ( 1.6 mL, 16.7 mmol) was added. The reaction mixture was heated to 70°C and stirred for 2.5 hours. The volatiles were removed in vacuo and the crude material was directly purified by flash chromatography on silica gel (0-50percent EtOAc/ heptanes) to afford the title compound as an off-white solid (1.31 g, 87percent yield). MS (ESI) m/e (M+H+): 269.73
81% With tetrachloromethane; triphenylphosphine In 1,2-dichloro-ethane at 70℃; for 1 h; The Preparation of Compound 12:
Compound 12F (1.6 g, 6.3 mmol), triphenylphosphine (3.33 g, 12.6 mmol) and tetrachloromethane (2.93 g, 18.9 mmol) were mixed in 1,2-dichloroethane (1,2-DCE, 64 mL), heated to 70° C. for 1 hour. The reaction was monitored via TLC (DCM/Methanol=10:1). The reaction mixture was concentrated and purified by silica gel chromatography to obtain a purified compound 12 (1.38 g, yield: 81percent) as a light yellow solid.
81% With tetrachloromethane; triphenylphosphine In 1,2-dichloro-ethane at 70℃; for 1 h; Compound 12F (1.6 g, 6.3 mmol), triphenylphosphine (3.33 g, 12.6 mmol) and tetrachloromethane (2.93 g, 18.9 mmol) were mixed in 1,2-dichloroethane (1,2-DCE, 64 mL), heated to 70° C. for 1 hour. The reaction was monitored via TLC (DCM/Methanol=10:1). The reaction mixture was concentrated and purified by silica gel chromatography to obtain a purified compound 12 (1.38 g, yield: 81percent) as a light yellow solid.

Reference: [1] Patent: US2014/275120, 2014, A1, . Location in patent: Paragraph 0160; 0161
[2] Patent: WO2011/29842, 2011, A1, . Location in patent: Page/Page column 40-41
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[4] Patent: US2016/75708, 2016, A1, . Location in patent: Paragraph 0086; 0092
[5] Patent: KR2015/139962, 2015, A, . Location in patent: Paragraph 0118-0119; 0131-0132
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Reference: [1] Patent: WO2010/66684, 2010, A2, . Location in patent: Page/Page column 112-113
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9273 - 9285
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Reference: [1] Patent: WO2011/29842, 2011, A1,
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9273 - 9285
[5] Patent: US2016/75708, 2016, A1,
[6] Patent: KR2015/139962, 2015, A,
  • 4
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Reference: [1] Patent: WO2011/29842, 2011, A1,
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
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Reference: [1] Patent: WO2011/29842, 2011, A1,
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
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Reference: [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
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Reference: [1] Patent: US2016/75708, 2016, A1,
[2] Patent: KR2015/139962, 2015, A,
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Reference: [1] Patent: US2016/75708, 2016, A1,
[2] Patent: KR2015/139962, 2015, A,
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