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[ CAS No. 74124-79-1 ]

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CAS No. :74124-79-1 MDL No. :MFCD00009767
Formula : C9H8N2O7 Boiling Point : 383.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :256.17 g/mol Pubchem ID :676246
Synonyms :

Safety of [ 74124-79-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P310-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 74124-79-1 ]

  • Upstream synthesis route of [ 74124-79-1 ]
  • Downstream synthetic route of [ 74124-79-1 ]

[ 74124-79-1 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 16867-03-1 ]
  • [ 74124-79-1 ]
  • [ 60832-72-6 ]
Reference: [1] Synthetic Communications, 1982, vol. 12, # 3, p. 213 - 218
  • 2
  • [ 38875-53-5 ]
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  • [ 148038-83-9 ]
Reference: [1] Patent: WO2004/35549, 2004, A1, . Location in patent: Page 200
  • 3
  • [ 4316-98-7 ]
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  • [ 37527-48-3 ]
YieldReaction ConditionsOperation in experiment
78% for 16 h; Heating / reflux Synthesis 20-1 -A; 6-Chloro-7H-purin-8(9H)-one; NXrNH2 A mixture of 4-chloropyrimidine-2,3-diamine (36 mg, 0.25 mmol) and di(/V-succinimidyl)carbonate (128 mg, 0.50 mmol) in acetonitrile (10 mL) was refluxed for 16 hours. The solids formed were collected, washed with acetonitrile (2 x 5 mL) and dried, to give the title compound as a light yellow powder (33 mg, 78percent).1H NMR (500 MHz, de-DMSO) δ 8.35 (1 H, s), 11.90 (2H, s, broad); LC-MS (2) R1 1.96 min; m/z (ESI) 171 [MH+].
Reference: [1] Patent: WO2008/75007, 2008, A1, . Location in patent: Page/Page column 113
  • 4
  • [ 74124-79-1 ]
  • [ 13734-34-4 ]
  • [ 3674-06-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5559 - 5562
  • 5
  • [ 74124-79-1 ]
  • [ 1142-20-7 ]
  • [ 3401-36-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5559 - 5562
  • 6
  • [ 74124-79-1 ]
  • [ 100-51-6 ]
  • [ 13139-17-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 1999, vol. 34, # 7-8, p. 625 - 638
[2] Patent: WO2008/64218, 2008, A2, . Location in patent: Page/Page column 72; 83-85; 86-87; 98-99; 125
  • 7
  • [ 6066-82-6 ]
  • [ 28920-43-6 ]
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  • [ 102774-86-7 ]
YieldReaction ConditionsOperation in experiment
95 kg With tributyl-amine In tetrahydrofuran at -2 - 5℃; Large scale From the reactor solid feed port one - time investment HosuL43. 8Kg (l. 25KmOl),With stirring,So that the kettle liquid at -2 ° C ~ 0 ° C.The tributylamine300Kg (l. 62 kP)And tetrahydrofuran450Kg into the high slot,After mixing,In 10 ~ llhr slowly added to the reactor in the reaction,The amount of added per hour for the 50 ~ 57Kg;And keep the kettle temperature not to exceed 5 ° C,Because of the exothermic reaction,After adding tributylamine in tetrahydrofuran solution,The reaction vessel was allowed to warm to room temperature and the reaction was continued for 7.5 h.A large amount of white solid crystals were observed to be precipitated by DSC from the reaction vessel.(3) filtered DSC crude: the reactor material in lhr evenly introduced into a fully enclosed centrifuge in N2Under the protection of throwing dry, and then twice the introduction of about 0 ° C tetrahydrofuran solvent 100Kg in the centrifuge rinse, throw dry,The DSC wet goods 120Kg. The wet goods in a vacuum oven at 40 ~ 45 ° C drying 7 ~ 8hr to constant weight, get out of the white crystalline powder 95Kg; HPLC analysis of 99. 1percent. The resulting filtrate was centrifuged to proceed to the next step. (3) filtered to obtain DSC crude: the reactor material in 1hr evenly introduced into a fully enclosed centrifuge, in the N2Under the protection of throwing dry, and then twice the introduction of about 0 ° C tetrahydrofuran solvent 100Kg in the centrifuge rinse, throw dry, get DSC wet goods 120Kg.The wet product in a vacuum oven at 40 ~ 45 dry 7 ~ 8hr to constant weight, get out of the white crystalline powder 95Kg; HPLC analysis of 99.1percent.The resulting filtrate was centrifuged to proceed to the next step.(4) The centrifugal filtrate in step (3) is combined with two washing solvents and introduced into a 2000L distilling apparatus. The tetrahydrofuran solvent is removed at a vacuum control temperature of 0 to 5 DEG C, and the inside temperature of the kettle is kept at 40 to 42 DEG C .After the tetrahydrofuran was removed, 230 kg of dichloroethane was introduced, stirred at 40-50 ° C for 0.5 hr, and washed with 160 kg of water 3 times. The phases were separated and the dichloromethane was introduced into a 500 L autoclave.
Reference: [1] Patent: CN104030962, 2016, B, . Location in patent: Paragraph 0036-0041
  • 8
  • [ 6066-82-6 ]
  • [ 32315-10-9 ]
  • [ 74124-79-1 ]
Reference: [1] Synthesis, 1993, # 1, p. 103 - 106
[2] Synthetic Communications, 1998, vol. 28, # 21, p. 4019 - 4024
[3] Synthetic Communications, 2005, vol. 35, # 24, p. 3119 - 3121
  • 9
  • [ 6066-82-6 ]
  • [ 503-38-8 ]
  • [ 74124-79-1 ]
Reference: [1] Patent: US4341707, 1982, A,
  • 10
  • [ 74124-79-1 ]
  • [ 55750-53-3 ]
  • [ 55750-63-5 ]
YieldReaction ConditionsOperation in experiment
70% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 1 h; Inert atmosphere 6-Maleimidohexanoic acid N-hydroxysuccinimide ester 4. Sodium bicarbonate (0.0512 g, 0.483 mmol ) was added to a solution of 6-maleimidocaproic acid (0.211 g, 1.000 mmol) in DI water (10 mL). After the reagents were dissolved in DI water, the DI water was evaporated by blowing with air. The resulting solid was dissolved in anhydrous DMF (3 mL) and the solution was cooled to 0 °C. Disuccinimide carbonate (0.282 g, 1.10 mmol) was added into the solution and the reaction was stirred at 0 °C for 1 h. CH2C12 (25 mL) was added into reaction which was then washed with water (3 x 10 mL). The resulting organic layer was dried over Na2S04, concentrated under reduced pressure, and purified by flash chromatography using a pre-packed 25 g silica column [solvent A: MeOH; solvent B: CH2C12; gradient: 0percentA / 100percentB (1 CV), 0percentA / 100percentB→ 2percentA / 98percentB (10 CV), 2percentA / 98percentB (2 CV); flow rate: 25 mL/min; monitored at 210 and 280 nm] to afford ester 4 (0.215 g, 0.697 mmol, 70percent yield) as a light yellow liquid. [000194] NMR (500 MHz, CDC13) 66.69 (2H, s), 3.53 (2H, t, J= 7.1 Hz), 2.83 (4H, s), 2.60 (2H, t, .7=7.4 Hz), 1.78 (2H,p, .7=7.5 Hz), 1.63 (2H,p, .7=7.4 Hz), 1.41 (2H,p,J=7.6 Hz). [000195] 13CNMR(125 MHz, CDC13) δ 170.9, 169.2, 168.5, 134.2,37.5,30.8,28.1,25.9,25.7,24.1.
Reference: [1] Journal of the American Chemical Society, 1994, vol. 116, # 14, p. 6101 - 6106
[2] Patent: WO2017/66668, 2017, A1, . Location in patent: Paragraph 000193-000195
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  • [ 55750-63-5 ]
Reference: [1] Biochemical Pharmacology, 2007, vol. 73, # 5, p. 620 - 631
[2] Patent: WO2007/90094, 2007, A2, . Location in patent: Page/Page column 35; 4/9
  • 12
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  • [ 1119-62-6 ]
  • [ 57757-57-0 ]
Reference: [1] Journal of Mass Spectrometry, 2011, vol. 46, # 1, p. 1 - 11
  • 13
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  • [ 74-89-5 ]
  • [ 18342-66-0 ]
  • [ 96-31-1 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 42, p. 4569 - 4572
  • 14
  • [ 143-07-7 ]
  • [ 74124-79-1 ]
  • [ 14565-47-0 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 1 h; Lauric acid (1.2 g, 5.99 mmol, 1 eq) is dissolved in N, N-dimethylformamide (DMF, 70 ml). N, N-disuccinimidyl carbonate (DSC, 4.6 g, 17.97 mmol, 3 eq) and N, N-diisopropylethylamine Hunig base, 10.2 ml, 59.91 mmol, 10 eq), and the mixture was stirred at 40 ° C for 1 hour. After completion of the reaction, the compound was lyophilized to obtain Compound 2-1 (2.1 g, 100percent)
Reference: [1] Patent: KR101871897, 2018, B1, . Location in patent: Paragraph 0138; 0139; 0141; 0142
  • 15
  • [ 74124-79-1 ]
  • [ 1138-80-3 ]
  • [ 2899-60-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5559 - 5562
  • 16
  • [ 74124-79-1 ]
  • [ 2483-46-7 ]
  • [ 30189-36-7 ]
Reference: [1] Heterocycles, 1981, vol. 15, # 1, p. 467 - 468
  • 17
  • [ 74124-79-1 ]
  • [ 96-41-3 ]
  • [ 128595-07-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 1, p. 110 - 115
[2] Synlett, 2011, # 10, p. 1454 - 1458
  • 18
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  • [ 18982-54-2 ]
  • [ 128611-93-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 1, p. 110 - 115
  • 19
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  • [ 3845-64-5 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 4008 - 4017
  • 20
  • [ 74124-79-1 ]
  • [ 107-18-6 ]
  • [ 135544-68-2 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16502 - 16508
  • 21
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  • [ 58-85-5 ]
  • [ 35013-72-0 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 49, p. 9859 - 9866
[2] ACS Combinatorial Science, 2017, vol. 19, # 12, p. 763 - 769
  • 22
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  • [ 2916-68-9 ]
  • [ 78269-85-9 ]
YieldReaction ConditionsOperation in experiment
84% With triethylamine In acetonitrile at 20℃; for 3 h; Compound 41; TEA (21.9 mL, 155.6 mmol, 3.0 eq.) was added to 2-trimethylsilanyl- ethanol (7.4 mL, 51.88 mmol, 1.0 eq.) in 260 mL MeCN, followed by di- succinimidyl carbonate (20 g, 1.5 eq.). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and extracted using EtOAc/ saturated NaHCO3. The organic layer was concentrated after dried over Na2SO4. Ether (100 mL) was added to the residue to form a precipitate. The precipitate was filtered and dried to give Compound 41 as a white solid (11.1 g, 84percent). 1H NMR (300 MHz, CDCl3): δ 4.42 (t, 3 H), 2.82 (s, 4 H), 1.16 (t, 2 H), 0.1 (s, 9 H).
82% With triethylamine In acetonitrile at 25℃; for 16 h; Example 5; methyl (l-l- ( {2- [ (2, 36)-3-amino-2-hydroxy-4-phenylbutyl]-2- benzylhydrazino} carbonyl)-2, 2-dimethylpropylcarbamate; Example 5A; 1- (f [2- (trimethylsilyl) ethoxy] carbonyl} oxy)-2, 5-pyrrolidinedione; Trimethylsilylethanol (7.4 mL, 52 mmol) was dissolved in acetonitrile (260 mL) and treated with disuccinimoyl carbonate (20 g, 1.5 equivalents) and triethylamine (33 mL, 3 equivalents) at 25°C for 16h. The solvents were evaporated, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was separated and washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue was triturated with ether to form a solid which was filtered and dried to give 11.12 g (82percent) of the title compound.
82% With triethylamine In acetonitrile EXAMPLE 5A
1-([2-(trimethylsilyl)ethoxy]carbonyl}oxy)-2,5-pyrrolidinedione
Trimethylsilylethanol (7.4 mL, 52 mmol) was dissolved in acetonitrile (260 mL) and treated with disuccinimoyl carbonate (20 g, 1.5 equivalents) and triethylamine (33 mL, 3 equivalents) at 25° C. for 16 h.
The solvents were evaporated, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was separated and washed with brine, dried over sodium sulfate, filtered and concentrated.
The crude residue was triturated with ether to form a solid which was filtered and dried to give 11.12 g (82percent) of the title compound.
Reference: [1] Patent: WO2008/11117, 2008, A2, . Location in patent: Page/Page column 491
[2] Patent: WO2005/61487, 2005, A1, . Location in patent: Page/Page column 115
[3] Patent: US2005/159469, 2005, A1, . Location in patent: Page/Page column 59
  • 23
  • [ 74124-79-1 ]
  • [ 156928-09-5 ]
  • [ 253265-97-3 ]
YieldReaction ConditionsOperation in experiment
90% With pyridine In tert-butyl methyl ether at 25 - 40℃; for 62 h; 26.3 g of tert-butyl methyl ether,35.09 g (135 mmol) of di (N-succinimidyl) carbonate,And 20.00 g (the content of the compound (II-1): 73.0percent) of the compound (II-1) and the compound (III-2) obtained in the same manner as in Example 2 were mixed at room temperature And the temperature was raised to 40 ° C. 11.89 g (150 mmol) of pyridine was added dropwise to the obtained solution at 40 ° C., and the mixture was stirred at 40 ° C. for 22 hours. The whole amount of the solution was cooled to 20 ° C., 73.0 g of 2-propanol was added dropwise at 20 ° C. to precipitate compound (I-1), cooled to 0 to 5 ° C. and then cooled to 0 to 5 ° C. for 19 hours Followed by stirring.The precipitated compound (I-1) was filtered and washed to obtain 27.83 g of compound (I-1) (content: 97.8percent, yield 90percent, enantiomeric excess of compound (I-1) Rate> 99.9percent ee). 30.0 g of tert-butylmethyl ether, 11.87 g of the compound (II-0)(The diastereomer ratio of the compound (II-1) to the 3S, 3aS, 6aR-OH form: 91.1 / 8.9 containing 84.3percent diastereomer) and the enzyme (CHIRAZYME L-2c, -flyo, manufactured by Roche Diagnostics) was added to the mixture at a temperature of 25 ° C. 3.31 g (38.4 mmol) of vinyl acetate was added dropwise to the mixture,After stirring at 25 ° C. for 40 hours, insoluble matter was filtered off.The filtrate was concentrated to obtain 12.73 g of a mixture containing compound (II-1) and compound (III-2) (yield of compound (II-1): 90percent 3S, 3aS, 6aR-OH isomer: 100.0 / 0.0). (II-1) and the compound (III-2) obtained in the same manner as in Example 2, 26.3 g of tert-butyl methyl ether, 35.09 g (135 mmol) of di (N-succinimidyl carbonate) And 20.00 g of the compound (II-1) in an amount of 73.0percent) were mixed at room temperature, and the mixture was heated to 40 ° C. To the resulting solution, 11.89 g (150 mmol) of pyridine was added dropwise at 40 ° C. And the mixture was stirred for 22 hours at 40 ° C. The total amount of the solution was cooled to 20 ° C. and 73.0 g of 2-propanol was dropwise added at 20 ° C. to precipitate the compound (I-1) and cooled to 0 to 5 ° C. , And the mixture was stirred for 19 hours at 0 to 5 ° C. The precipitated compound (I-1) was filtered,(Yield: 97.8percent, yield: 90percent, enantiomer excess of compound (I-1)> 99.9percent ee) was obtained by filtration and washing with water to obtain 27.83 g of compound (I-1).
Reference: [1] Patent: JP2016/150901, 2016, A, . Location in patent: Paragraph 0016; 0017; 0023; 0024
[2] Journal of Organic Chemistry, 2004, vol. 69, # 23, p. 7822 - 7829
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 10, p. 1874 - 1880
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1813 - 1822
[5] Patent: WO2010/23322, 2010, A1, . Location in patent: Page/Page column 29
[6] Patent: US2008/85918, 2008, A1, . Location in patent: Page/Page column 18; Sheet 3
[7] Patent: WO2011/92687, 2011, A1, . Location in patent: Page/Page column 31
[8] Patent: WO2016/207907, 2016, A1, . Location in patent: Page/Page column 23
[9] Organic Process Research and Development, 2017, vol. 21, # 1, p. 98 - 106
[10] Patent: WO2007/126812, 2007, A2, . Location in patent: Page/Page column 41
[11] Patent: WO2008/133734, 2008, A2, . Location in patent: Page/Page column 28-29
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Reference: [1] Patent: EP2883858, 2015, A1, . Location in patent: Paragraph 0171-0173
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  • [ 108-05-4 ]
  • [ 74124-79-1 ]
  • [ 109789-19-7 ]
  • [ 253265-97-3 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 1, p. 279 - 283
  • 26
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Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 9, p. 1615 - 1620
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