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[ CAS No. 167408-67-5 ] {[proInfo.proName]}

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Product Details of [ 167408-67-5 ]

CAS No. :167408-67-5 MDL No. :MFCD04967381
Formula : C8H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :MFRDTCKJOFHQDZ-UHFFFAOYSA-N
M.W :170.16 Pubchem ID :16227056
Synonyms :

Safety of [ 167408-67-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 167408-67-5 ]

* 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 [ 167408-67-5 ]

[ 167408-67-5 ] Synthesis Path-Downstream   1~56

  • 1
  • [ 553-90-2 ]
  • [ 765-43-5 ]
  • [ 167408-67-5 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: Dimethyl oxalate; Cyclopropyl methyl ketone With methanol; natrium at 0 - 20℃; Reflux; Stage #2: With sulfuric acid In diethyl ether; lithium hydroxide monohydrate Synthesis of compound 1 Na (14.67g, 0.64mol) was dissolved in dry MeOH (0.8L) and a solution of cyclo- propylmethylketone (50g, 0.59mol) and dimethyloxalate (70.2g, 0.59mol) in dry MeOH (0.2L) was added dropwise at 0°C. The reaction mixture was stirred at r.t. 24h and reflux overnight. Water (0.5L) was added and the methanol was removed under reduced pressure. The aqueous solution was washed with Et21H-NMR (CDCI3): δ= 14.61 (br, 1 H), 6.84 (s, 1 H), 3.90 (s, 3H), 1 .95-1 .82 (m, 1 H), 1.26- 1 .20 (m, 2H), 1 .10-1 .00 (m, 2H).
55% With methanol; natrium at 0 - 20℃; Reflux; Inert atmosphere; Synthesis of compound 10 Na (14.67 g, 0.64 mol) was dissolved in dry methanol (0.8 L) and a solution of cyclopropylmethylketone 5 (50 g, 0.59 mol) and dimethyloxalate (70.2 g, 0.59 mol) in dry MeOH (0.2 L) was added dropwise at 0°C. The reaction mixture was stirred at room temperature 24h and reflux overnight. Water (0.5 L) was added and the methanol was removed under reduced pressure. The aqueous solution was washed with Et.20 (150 ml_), acidified to pH=2 with 2M H2S04 and extracted with Et20 (diethylether, 3x150 ml_). The organic layer was dried over MgS04 and concentrated to dryness, to yield compound 10 (55.6 g, 55%), which was used without further purification. H-NMR (CDCIs): δ= 14.61 (br, 1 H), 6.84 (s, 1 H), 3.90 (s, 3H), 1 .95-1 .82 (m, 1 H), 1 .26- 1 .20 (m, 2H), 1 .10-1 .00 (m, 2H).
5 g Stage #1: Cyclopropyl methyl ketone With sodium methoxide In methanol at 20℃; for 0.25h; Stage #2: Dimethyl oxalate In methanol at 20℃; for 16h; O1 -Cvclopropyl-2,4-dioxo-butyric acid methyl ester To a solution of cyclopropyl methyl ketone (5 g, 59.4 mmol) in MeOH (75 ml.) was added sodium methoxide (4.8 g, 54.0 mmol) at rt. After a 15 min stirring, dimethyl oxalate (7 g, 59.4 mmol) was added. The reaction mixture was stirred for 16 h at rt and concentrated. The residue was taken up in a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The organic layers were dried (Na2S04), filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5) to provide 5 g of the title compound. Rf= 0.59 (hexane/EtOAc, 4:1 ); H NMR (300 MHz, CDCI3) δ ppm 1.00-1.30 (m, 4 H), 1.80-1.95 (m, 1 H), 3.85 (s, 3 H), 6.48 (s, 1 H), 14.2-15.0 (br. s, 1 H).
With potassium-t-butoxide In tetrahydrofuran; toluene at 20℃;
With sodium methoxide In methanol at 0 - 20℃; for 12h; Inert atmosphere; 4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 1. To a solution of acetone (6a, 580 mg, 10 mmol) and dimethyloxalate (7, 1.18 g, 10 mmol) in anhydrous methanol (50 mL) was degassed with argon and cooled to 0 °C in an ice bath. 30% sodium methanolate in methanol (20 mmol) was added dropwise into the coldsolution and the mixture was allowed to warm to room temperature. After 12 h, the resultant mixture was quenched with conc. HCl (5 mL)and concentrated in vacuo. The residue was then diluted with water (50 mL) and extracted with EA (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give methyl acetopyruvate (8a) which was directly used in the next step without further purification.
With sodium methoxide In methanol at 0 - 20℃; for 12h; Inert atmosphere; 4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 1. To a solution of acetone (6a, 580 mg, 10 mmol) and dimethyloxalate (7, 1.18 g, 10 mmol) in anhydrous methanol (50 mL) was degassed with argon and cooled to 0 °C in an ice bath. 30% sodium methanolate in methanol (20 mmol) was added dropwise into the coldsolution and the mixture was allowed to warm to room temperature. After 12 h, the resultant mixture was quenched with conc. HCl (5 mL)and concentrated in vacuo. The residue was then diluted with water (50 mL) and extracted with EA (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give methyl acetopyruvate (8a) which was directly used in the next step without further purification.

  • 2
  • [ 14678-02-5 ]
  • [ 167408-67-5 ]
  • [ 931997-41-0 ]
YieldReaction ConditionsOperation in experiment
97% With acetic acid for 2h; Reflux; Synthesis of compound 4A mixture of compound 1 (3g, 17.6mmol) and 5-amino-3-methylisoxazole (1 .73g, 17.6mmol) in AcOH (44mL) was stirred at reflux for 2h. The reaction mixture was poured into ice/water (100ml_). The solid formed was collected by filtration and dried under high vacuum. 3.9g (97%) of compound 4 were obtained.1H-NMR (CDCI3): δ= 7.69 (s, 1 H), 4.02 (s, 3H), 2.69 (s, 3H), 2.26-2.15 (m, 1 H), 1 .28- 1 .21 (m, 2H), 1 .19-1 .1 1 (m, 2H).MS: m/z= 233 [M+H]+
  • 3
  • [ 167408-67-5 ]
  • [ 822-63-9 ]
  • [ 1356475-42-7 ]
YieldReaction ConditionsOperation in experiment
82% With acetic acid for 2h; Reflux; Synthesis of compound 20 A mixture of compound 1 (17g, 0.1 mol) and 5-amino-isoxazol-3-one (10g,0.1 mol) in acetic acid (AcOH) (100ml_) was stirred at reflux for 2h. The reaction mixture was poured into ice/water (200ml_). The solid formed was collected by filtration and dried under high vacuum. 19g (82%) of compound 20 were obtained.1H-NMR (CDCI3): δ= 10.30 (bs, 1 H), 7.69 (s, 1 H), 4.12 (s, 3H), 2.27-2.20 (m, 1 H), 1.29- 1 .22 (m, 2H), 1 .21 -1 .12 (m, 2H).MS: m/z= 235 [M+H]+
82% With acetic acid for 2h; Reflux; Synthesis of compound 11 A mixture of compound 10 (17 g, 0.1 mol) and 5-amino-isoxazol-3-one (10 g, 0.1 mol) in acetic acid (AcOH) (100 ml.) was stirred at reflux for 2h. The reaction mixture was poured into ice/water (200 ml_). The solid formed was collected by filtration and dried under high vacuum. 19 g (82%) of compound 11 were obtained. H-NMR (CDCIs): δ= 10.30 (bs, 1 H), 7.69 (s, 1 H), 4.12 (s, 3H), 2.27-2.20 (m, 1 H), 1 .29- 1 .22 (m, 2H), 1 .21 -1.12 (m, 2H); MS: m/z= 235 [M+H]+
  • 4
  • [ 167408-67-5 ]
  • [ 1356475-44-9 ]
  • [ 1356475-45-0 ]
YieldReaction ConditionsOperation in experiment
72% With acetic acid for 2h; Reflux; Synthesis of compound 27A mixture of compound 1 (1 1 .5g, 0.07mol) and 26 (13.8g, 0.07mol) in AcOH (150ml_) was stirred at reflux for 2h. The reaction mixture was poured into ice/water (200ml_). The solid formed was collected by filtration and dried under high vacuum. 16.5g (72%) of compound 27 were obtained.1H-NMR (CDCb): δ= 7.68 (s, 1 H), 7.32 (s, 5H), 5.03 (s, 2H), 4.60 (s, 2H), 3.95 (s, 3H), 2.26-2.20 (m, 1 H), 1 .30-1.25 (m, 2H), 1 .20-1 .12 (m, 2H).MS: m/z= 339 [M+H]+
72% With acetic acid for 2h; Reflux; Synthesis of compound 26 A mixture of compound 10 (1 1.5 g, 0.07 mol) and 25 (13.8 g, 0.07 mol) in AcOH (150 ml.) was stirred at reflux for 2h. The reaction mixture was poured into ice/water (200 ml_). The solid formed was collected by filtration and dried under high vacuum. 16.5 g (72%) of compound 26 were obtained. H-NMR (CDCIs): δ= 7.68 (s, 1 H), 7.32 (s, 5H), 5.03 (s, 2H), 4.60 (s, 2H), 3.95 (s, 3H), 2.26-2.20 (m, 1 H), 1 .30-1.25 (m, 2H), 1 .20-1 .12 (m, 2H); MS: m/z= 339 [M+H]+
  • 5
  • [ 167408-67-5 ]
  • [ 119162-59-3 ]
  • [ 1356473-94-3 ]
YieldReaction ConditionsOperation in experiment
79% With acetic acid for 4h; Reflux; Synthesis of compound 2 A mixture of compound 1 (0.9g, 5.3mmol) and 5-amino-3-(2- phenylethyl)isoxazole (1.0g, 5.3mmol) in AcOH (16ml_) was stirred at reflux for 4h. The reaction mixture was poured into ice/water (100ml_). The solid formed was collected by filtration and dried under high vacuum. 1.5g (79%) of compound 2 were obtained.1H-NMR (CDCI3): δ= 7.62 (s, 1 H), 7.27-7.1 1 (m, 5H), 3.93 (s, 3H), 3.43-3.37 (m, 2H) 3.03-2.97 (m, 2H), 2.22-2.10 (m, 1 H), 1 .24-1 .17 (m, 2H), 1 .13-1 .05 (m, 2H).MS: m/z= 323[M+H]+, 345 [M+Na]+
  • 6
  • [ 167408-67-5 ]
  • [ 100-52-7 ]
  • [ 74-89-5 ]
  • C15H15NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; benzaldehyde; methylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 7
  • [ 167408-67-5 ]
  • [ 104-88-1 ]
  • [ 75-04-7 ]
  • C16H16ClNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 4-chlorobenzaldehyde; ethylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 8
  • [ 167408-67-5 ]
  • [ 123-11-5 ]
  • [ 1003-03-8 ]
  • C20H23NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 4-methoxy-benzaldehyde; Cyclopentamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 9
  • [ 167408-67-5 ]
  • [ 10031-82-0 ]
  • [ 108-91-8 ]
  • C22H27NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 4-ethoxybenzaldehyde; cyclohexylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 10
  • [ 498-62-4 ]
  • [ 167408-67-5 ]
  • [ 109-85-3 ]
  • C15H17NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 2-methoxyethylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 11
  • [ 498-62-4 ]
  • [ 167408-67-5 ]
  • [ 100-36-7 ]
  • C18H24N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; N,N-diethylethylenediamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 12
  • [ 2038-03-1 ]
  • [ 498-62-4 ]
  • [ 167408-67-5 ]
  • C18H22N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(2-AMINOETHYL)MORPHOLINE; 3-thiophene carboxaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 13
  • [ 498-62-4 ]
  • [ 3731-52-0 ]
  • [ 167408-67-5 ]
  • C18H16N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 3-Aminomethylpyridine; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 14
  • [ 498-62-4 ]
  • [ 5036-48-6 ]
  • [ 167408-67-5 ]
  • C18H19N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 3-(1H-imidazol-1-yl)propan-1-amine; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 15
  • [ 140-31-8 ]
  • [ 498-62-4 ]
  • [ 167408-67-5 ]
  • C18H23N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: aminoethylpiperazine; 3-thiophene carboxaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 16
  • [ 498-62-4 ]
  • [ 167408-67-5 ]
  • [ 98-16-8 ]
  • C18H16N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 3-trifluoromethylaniline With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 17
  • [ 498-62-4 ]
  • [ 6336-68-1 ]
  • [ 167408-67-5 ]
  • C23H24N2O5S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 4-(piperidin-1-ylsulfonyl)aniline; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 18
  • [ 504-29-0 ]
  • [ 498-62-4 ]
  • [ 167408-67-5 ]
  • C17H14N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-aminopyridine; 3-thiophene carboxaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 19
  • [ 498-62-4 ]
  • [ 109-12-6 ]
  • [ 167408-67-5 ]
  • C16H13N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 2-aminopyrimidine; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 20
  • [ 498-62-4 ]
  • [ 5049-61-6 ]
  • [ 167408-67-5 ]
  • C16H13N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 2-Aminopyrazine; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 21
  • [ 498-62-4 ]
  • [ 3829-80-9 ]
  • [ 167408-67-5 ]
  • C18H16N2O5S2 [ No CAS ]
  • 22
  • [ 498-62-4 ]
  • [ 28466-21-9 ]
  • [ 167408-67-5 ]
  • C18H19N3O3S [ No CAS ]
  • 23
  • [ 498-62-4 ]
  • [ 1072-67-9 ]
  • [ 167408-67-5 ]
  • C16H14N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 5-methylisoxazol-3-ylamine; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 24
  • [ 96-50-4 ]
  • [ 498-62-4 ]
  • [ 167408-67-5 ]
  • C15H12N2O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-thiazolylamine; 3-thiophene carboxaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 25
  • [ 498-62-4 ]
  • [ 2289-75-0 ]
  • [ 167408-67-5 ]
  • C17H16N2O3S2 [ No CAS ]
  • 26
  • [ 498-62-4 ]
  • [ 2536-91-6 ]
  • [ 167408-67-5 ]
  • C20H16N2O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 6-methylbenzothiazol-2-ylamine; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 27
  • [ 498-62-4 ]
  • [ 17647-70-0 ]
  • [ 167408-67-5 ]
  • C15H13N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 3-amino-4-methylfurazan; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 28
  • [ 498-62-4 ]
  • [ 108-33-8 ]
  • [ 167408-67-5 ]
  • C15H13N3O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 5-methyl-1,3,4-thiadiazol-2-amine; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 29
  • [ 498-62-4 ]
  • [ 6913-13-9 ]
  • [ 167408-67-5 ]
  • C15H13N3O3S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 5-amino-3-methylthio-1,2,4-thiadiazole; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 30
  • [ 498-62-4 ]
  • [ 167408-67-5 ]
  • [ 150-13-0 ]
  • C19H15NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 4-amino-benzoic acid With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 31
  • [ 498-62-4 ]
  • [ 1197-55-3 ]
  • [ 167408-67-5 ]
  • [ 1050952-63-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-thiophene carboxaldehyde; 4-aminophenylacetic acid; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 32
  • [ 498-62-4 ]
  • [ 93-85-6 ]
  • [ 167408-67-5 ]
  • [ 1051082-87-1 ]
  • 33
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 74-89-5 ]
  • C13H15N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; methylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 34
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 75-04-7 ]
  • C14H17N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; ethylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 35
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 1003-03-8 ]
  • C17H21N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; Cyclopentamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 36
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 108-91-8 ]
  • C18H23N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; cyclohexylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 37
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 109-85-3 ]
  • C15H19N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 2-methoxyethylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 38
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 5332-73-0 ]
  • C16H21N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 3-methoxypropylamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 39
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 106-49-0 ]
  • C18H18N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; <i>p</i>-toluidine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 40
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 109-55-7 ]
  • C17H24N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; 1-amino-3-(dimethylamino)propane With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 41
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • [ 100-36-7 ]
  • C18H26N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester; N,N-diethylethylenediamine With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 42
  • [ 2038-03-1 ]
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • C18H24N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(2-AMINOETHYL)MORPHOLINE; 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 43
  • [ 3731-52-0 ]
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • C18H18N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-Aminomethylpyridine; 1-methylpyrazole-4-carbaldehyde; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 44
  • [ 25016-11-9 ]
  • [ 5036-48-6 ]
  • [ 167408-67-5 ]
  • C18H21N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 3-(1H-imidazol-1-yl)propan-1-amine; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 45
  • [ 3829-80-9 ]
  • [ 25016-11-9 ]
  • [ 167408-67-5 ]
  • C18H18N4O5S [ No CAS ]
  • 46
  • [ 25016-11-9 ]
  • [ 28466-21-9 ]
  • [ 167408-67-5 ]
  • C18H21N5O3 [ No CAS ]
  • 47
  • [ 25016-11-9 ]
  • [ 2289-75-0 ]
  • [ 167408-67-5 ]
  • C17H18N4O3S [ No CAS ]
  • 48
  • [ 25016-11-9 ]
  • [ 17647-70-0 ]
  • [ 167408-67-5 ]
  • C15H15N5O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methylpyrazole-4-carbaldehyde; 3-amino-4-methylfurazan; 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;
  • 49
  • [ 25016-11-9 ]
  • [ 93-85-6 ]
  • [ 167408-67-5 ]
  • C20H16N4O5S [ No CAS ]
  • 50
  • [ 167408-67-5 ]
  • [ 106-49-0 ]
  • [ 27258-33-9 ]
  • C19H19N3O3 [ No CAS ]
  • 51
  • [ 167408-67-5 ]
  • methyl 5-cyclopropylisoxazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With hydroxylamine hydrochloride In ethanol at 70℃; for 1h; 28 General procedure for preparation of methyl 5-cyclopropylisoxazole-3-carboxylate A mixture of methyl 4-cyclopropyl-2,4-dioxo-butanoate (900 mg, 5.3 mmol, 1.0 eq), hydroxylamine (1.1 g, 16 mmol, 3.0 eq, HC1 salt) in 10 mL of EtOH was stirred at 70 °C for 1 hour. The reactionmixture was concentrated under reduced pressure to give an oil. The oil was diluted with 10 mL of water and extracted twice with 16 mL of EtOAc. The combined organic layers were washed with 10 mL of brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give a colorless oil which was purified by column chromatography (Si02, eluting with a gradient of petroleum ether:ethyl acetate = 100:1 to 20:1) to give 175mg of methyl 5-cyclopropylisoxazole-3-carboxylate (1.05 mmol, 20% yield) as a colorless oil.
  • 52
  • [ 167408-67-5 ]
  • [ 108-94-1 ]
  • methyl 2-cyclopropyl-5,6,7,8-tetrahydroquinoline-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: cyclohexanone With ammonium acetate In 1,4-dioxane at 20℃; for 0.75h; Inert atmosphere; Green chemistry; Stage #2: 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester With chitosan In 1,4-dioxane at 80℃; for 18h; Inert atmosphere; Green chemistry; regioselective reaction;
  • 53
  • [ 167408-67-5 ]
  • 3-(2-(allyloxy)-4-bromo-6-fluorophenyl)-1H-pyrazol-5-amine [ No CAS ]
  • methyl 2-(2-(allyloxy)-4-bromo-6-fluorophenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% In ethanol at 80℃; for 3h; B Intermediate J9 : methyl 2-(2-(allyloxy)-4-bromo-6-fluorophenyl)-7-cyclopropyl- pyrazo lo [ 1 ,5 -a]pyrimidine-5 -carboxylate A mixture of J8 (14.4 g; 46.1 mmol) and Methyl 4-cyclopropyl-2,4-dioxobutanoate [167408-67-5] (8.26 g; 46.1 mmol) in EtOH (200 mL) was stirred at 80 °C for 3 h. The mixture was cooled to rt and a precipitate was formed. The precipitate was filtered and dried on the frit to give intermediate J9 as yellow solid (7.96 g, 38%).
  • 54
  • [ 167408-67-5 ]
  • [ 934-22-5 ]
  • [ 15164-44-0 ]
  • C21H16IN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 5-aminobenzimidazole; p-(iodophenyl)carboxaldehyde With acetic acid In ethanol at 80℃; for 0.333333h; Stage #2: 4-cyclopropyl-2,4-dioxo-butyric acid methyl ester In ethanol Heating; A solution of 4-iodobenzaldehyde (1.36 mg, 5.88 mmol) and 1H-benzo[d]imidazol-6- amine (782 mg, 1.0 eq.) in ethanol (10 mL) and acetic acid (0.5 mL) was heated at 80oC for 20 mins. Methyl 4-cyclopropyl-2,4-dioxobutanoate 1 (1.0 g, 1.0 eq.) was added dropwise and the reaction was heated overnight. The reaction was cooled to 0oC and compound 2 was collected by filtration and isolated as a brown solid (1.57 g, 55%).
  • 55
  • [ 167408-67-5 ]
  • 4-Hydrazino-N-methylbenzenemethanesulphonamide hydrochloride [ No CAS ]
  • 5-cyclopropyl-1-(4-((N-methylsulfamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 4-cyclopropyl-2,4-dioxobutanoate; 4-Hydrazino-N-methylbenzenemethanesulphonamide hydrochloride In ethanol at 85℃; for 12h; Stage #2: With lithium hydroxide monohydrate; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 20℃; for 2h; 4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 1. To a solution of acetone (6a, 580 mg, 10 mmol) and dimethyloxalate (7, 1.18 g, 10 mmol) in anhydrous methanol (50 mL) was degassed with argon and cooled to 0 °C in an ice bath. 30% sodium methanolate in methanol (20 mmol) was added dropwise into the coldsolution and the mixture was allowed to warm to room temperature. After 12 h, the resultant mixture was quenched with conc. HCl (5 mL)and concentrated in vacuo. The residue was then diluted with water (50 mL) and extracted with EA (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give methyl acetopyruvate (8a) which was directly used in the next step without further purification. Step 2. To a solution of 8a (118 mg, 1 mmol) and 4-hydrazino-N-methylbenzenemethanesulfonamide hydrochloride (9, 252 mg, 1 mmol)in anhydrous ethanol (10 mL) was stirred at 85 °C overnight. The reaction was allowed to cool to room temperature and concentrated. The crude material was purified by Isolera Biotage LPLC (PE/EA = 30%) to give a mixture of methyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (10a) and ethyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (11a) as a white solid. Step 3. To a solution of 10a and 11a (100mg) in 2:2:1 MeOH/THF/H2O (5mL) was added 1M LiOH (1mL) and stirred at room temperature. After 2h, the mixture was concentrated, diluted with water (5mL), acidified with 2M HCl (1mL) and filtered. The filtrate cake was washed with water and dried under vacuum to give the 12a (73mg) as a white solid.
Stage #1: methyl 4-cyclopropyl-2,4-dioxobutanoate; 4-Hydrazino-N-methylbenzenemethanesulphonamide hydrochloride In ethanol at 85℃; for 12h; Stage #2: With lithium hydroxide monohydrate; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 20℃; for 2h; 4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 1. To a solution of acetone (6a, 580 mg, 10 mmol) and dimethyloxalate (7, 1.18 g, 10 mmol) in anhydrous methanol (50 mL) was degassed with argon and cooled to 0 °C in an ice bath. 30% sodium methanolate in methanol (20 mmol) was added dropwise into the coldsolution and the mixture was allowed to warm to room temperature. After 12 h, the resultant mixture was quenched with conc. HCl (5 mL)and concentrated in vacuo. The residue was then diluted with water (50 mL) and extracted with EA (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give methyl acetopyruvate (8a) which was directly used in the next step without further purification. Step 2. To a solution of 8a (118 mg, 1 mmol) and 4-hydrazino-N-methylbenzenemethanesulfonamide hydrochloride (9, 252 mg, 1 mmol)in anhydrous ethanol (10 mL) was stirred at 85 °C overnight. The reaction was allowed to cool to room temperature and concentrated. The crude material was purified by Isolera Biotage LPLC (PE/EA = 30%) to give a mixture of methyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (10a) and ethyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (11a) as a white solid. Step 3. To a solution of 10a and 11a (100mg) in 2:2:1 MeOH/THF/H2O (5mL) was added 1M LiOH (1mL) and stirred at room temperature. After 2h, the mixture was concentrated, diluted with water (5mL), acidified with 2M HCl (1mL) and filtered. The filtrate cake was washed with water and dried under vacuum to give the 12a (73mg) as a white solid.
  • 56
  • [ 64-17-5 ]
  • [ 167408-67-5 ]
  • 4-Hydrazino-N-methylbenzenemethanesulphonamide hydrochloride [ No CAS ]
  • methyl 5-cyclopropyl-1-(4-((N-methylsulfamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate [ No CAS ]
  • ethyl 5-cyclopropyl-1-(4-((N-methylsulfamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 85℃; for 12h; 4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 2. To a solution of 8a (118 mg, 1 mmol) and 4-hydrazino-N-methylbenzenemethanesulfonamide hydrochloride (9, 252 mg, 1 mmol)in anhydrous ethanol (10 mL) was stirred at 85 °C overnight. The reaction was allowed to cool to room temperature and concentrated. The crude material was purified by Isolera Biotage LPLC (PE/EA = 30%) to give a mixture of methyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (10a) and ethyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (11a) as awhite solid.
at 85℃; for 12h; 4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 2. To a solution of 8a (118 mg, 1 mmol) and 4-hydrazino-N-methylbenzenemethanesulfonamide hydrochloride (9, 252 mg, 1 mmol)in anhydrous ethanol (10 mL) was stirred at 85 °C overnight. The reaction was allowed to cool to room temperature and concentrated. The crude material was purified by Isolera Biotage LPLC (PE/EA = 30%) to give a mixture of methyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (10a) and ethyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (11a) as awhite solid.
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