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[ CAS No. 67704-17-0 ] {[proInfo.proName]}

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Chemical Structure| 67704-17-0
Chemical Structure| 67704-17-0
Structure of 67704-17-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 67704-17-0 ]

CAS No. :67704-17-0 MDL No. :MFCD28967877
Formula : C9H10N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 194.19 Pubchem ID :-
Synonyms :

Safety of [ 67704-17-0 ]

Signal Word:Warning Class:
Precautionary Statements:P201-P202-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P308+P313-P330-P332+P313-P362+P364-P403+P233-P501 UN#:
Hazard Statements:H302-H315-H319-H335-H351 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 67704-17-0 ]

* 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 [ 67704-17-0 ]

[ 67704-17-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1877-71-0 ]
  • [ 67704-17-0 ]
YieldReaction ConditionsOperation in experiment
99% With fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 12.1 SYNTHETIC EXAMPLE 12; Synthesis of 3-carboxybenzoic [N'- (1- (1- (4-TERT-] butylphenyl)-3-methyl-5-oxo-1, 5-dihydropyrazol-4- ylidene)-ethyl)-hydrazide; 1) Synthesis of 3-methoxycarbonylbenzhydrazide The procedure in Synthetic Example 4 was followed using monomethyl isophthalate and tetramethylfluoroformamidinium hexafluorophosphate to 244.6 mg of a yellow solid (yield > 99%). [1H-NMR] (ppm in DMSO-d6) [5 =] 3.89 (s, 3H), 4.61 (bs, 2H), 7.62 (dd, 1H, J = 8.0 Hz, 8.0 Hz), 8.08 (dd, 2H, J = 1.8, 8.0 Hz), 8.42 (d, [1H, J =] 1.8 Hz), 9.98 (bs, 1H). LC/MS [M+ = 194 (0.] 51 min).
Multi-step reaction with 2 steps 1: 4-methyl-morpholine / dichloromethane / 1 h / 0 °C 2: hydrazine / dichloromethane / 2 h / 0 °C
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 20 °C 2: hydrogenchloride / ethyl acetate / 2 h / 0 - 20 °C
  • 2
  • [ 1459-93-4 ]
  • [ 67704-17-0 ]
YieldReaction ConditionsOperation in experiment
44.a Example 44. 3-S-5-CYCLOHEXYL-L- (3, 3-DIMETHYL-2-OXO-BUTYL)-2-OXO-1, 2-DIHYDRO-3H- 1, 3, 4-benzotriazepin-3-ylmethyl]-[1,3,4]oxadiazol-2-yl}-benzoic acid.; [0143] Step a. 3-(N'-{2-[5-Cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1, 2- DIHYDRO-3H-1, 3, 4-BENZOTRIAZEPIN-3-YL]-ACETYL}-HYDRAZINOCARBONYL)-BENZOIC acid methyl ester was obtained by the method used in the preparation of 3-{2-[5-cyclohexyl-1-(3, 3-dimethyl-2- oxo-butyl) -2-oxo-1,2-dihydro-3H-1, 3, 4-BENZOTRIAZEPIN-3-YL]-ACETYLAMINO}-BENZOIC acid methyl ester (Example 1) except that 3-hydrazinocarbonyl-benzoic acid methyl ester (prepared in two steps from isophthalic acid dimethyl ester) was used instead of 3-amino-benzoic acid methyl ester in step e.
With hydrazine In methanol at 60℃; for 48h;
  • 3
  • [ 35272-15-2 ]
  • [ 67704-17-0 ]
  • methyl 3-(2-(2-methylthiazole-4-carbonyl)hydrazine-1-carbonyl)benzoate [ No CAS ]
  • 4
  • [ 67704-17-0 ]
  • [ 80745-61-5 ]
  • methyl 3-(5-(4-iodobicyclo[2.2.2]octan-1-yl)-1,3,4-thiadiazol-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Stage #1: methyl 3-(hydrazinecarbonyl)benzoate; 4-iodobicyclo<2.2.2>octane-1-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 2h; Stage #2: With diphosphorus pentasulfide In tetrahydrofuran at 50℃; for 18h; 19.A.1; 19.A.2 Step A. Intermediate 19A. Preparation of methyl 3-(5-(4-iodobicyclo[2.2.2]octan-1-yl)-1,3,4-thiadiazol-2-yl)benzoate To a mixture of Intermediate 4B (0.24 g, 0.84 mmol), methyl 3-(hydrazinecarbonyl)benzoate (0.16 g, 0.84 mmol) (Bradner, J. E. et al. WO 2014/071247), TEA (0.18 mL, 1.3 mmol) and HOBT (0.039 g, 0.25 mmol) in DMF (6 mL) was added EDC (0.24 g, 1.3 mmol) and the resulting mixture was stirred. After 2 h, the reaction was diluted with water (50 mL) and extracted with EtOAc (2×25 mL). The organic phase was combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was dried in vacuo and taken onto the next step without characterization. Step 2: The product of Step 1 was dissolved in THF (5 mL), phosphorus pentasulfide (0.48 g, 2.2 mmol) was added and the reaction was stirred at 50° C. After 18 h, the reaction was cooled, filtered and the filtrate was concentrated. The crude product was purified by flash column chromatography (40 g silica gel cartridge; A=Hex, B=EtOAc; 20 min grad.; 0% B to 60% B; flow rate=40 mL/min). The pure fractions were combined, concentrated and dried in vacuo to afford the title compound (60 mg, 0.13 mmol, 16% yield) as a white solid. 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ 8.41 (t, J=1.5 Hz, 1H), 8.05 (td, J=7.9, 1.4 Hz, 2H), 7.48 (t, J=7.8 Hz, 1H), 3.85 (s, 3H), 2.58-2.50 (m, 6H), 2.17-2.05 (m, 6H). MS (ESI) 455 (M+H).
  • 5
  • [ 67704-17-0 ]
  • [ 80745-61-5 ]
  • methyl 3-(5-(4-iodobicyclo[2.2.2]octan-1-yl)-1,3,4-oxadiazol-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% Stage #1: methyl 3-(hydrazinecarbonyl)benzoate; 4-iodobicyclo<2.2.2>octane-1-carboxylic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In acetonitrile for 2h; Stage #2: With N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride In acetonitrile for 18h; Inert atmosphere; 18.A Step A. Intermediate 18A. Preparation of methyl 3-(5-(4-iodobicyclo[2.2.2]octan-1-yl)-1,3,4-oxadiazol-2-yl)benzoate To a mixture of Intermediate 4B (0.24 g, 0.84 mmol), methyl 3-(hydrazinecarbonyl) benzoate (0.16 g, 0.84 mmol) (Bradner, J. E. et al. WO 2014/071247) and DIEA (0.44 mL, 2.5 mmol) in MeCN (10 mL) was added TBTU (0.30 g, 0.92 mmol). After stirring 2 h, DIEA (0.29 mL, 1.7 mmol), followed by p-toluenesulfonyl chloride (0.48 g, 2.5 mmol) were successively added and the resulting reaction mixture was stirred under N2. After 18 h, the mixture was diluted with 1 M K2HPO4 (aq.) (50 mL) and extracted with EtOAc (2*25 mL). The organic phase was combined, washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography (40 g silica gel cartridge; A=Hex, B=EtOAc; 15 min grad.; 0% B to 100% B; flow rate=40 mL/min). The pure fractions were combined, concentrated and dried in vacuo to afford the title compound (0.063 g, 0.14 mmol, 17% yield) as a white solid. 1H NMR (500 MHz, DICHLOROMETHANE-d2) δ 8.69-8.60 (m, 1H), 8.31-8.19 (m, 2H), 7.69-7.60 (m, 1H), 3.99 (s, 3H), 2.70-2.61 (m, 6H), 2.24 (br d, J=8.3 Hz, 6H). MS (ESI) 439 (M+H).
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