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Chemical Structure| 36600-66-5
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Product Details of [ 36600-66-5 ]

CAS No. :36600-66-5 MDL No. :MFCD00013387
Formula : C10H16N2.xHCl Boiling Point : -
Linear Structure Formula :- InChI Key :VTESCYNPUGSWKG-UHFFFAOYSA-N
M.W : 200.71 (monohydrochloride basis) Pubchem ID :16217458
Synonyms :

Safety of [ 36600-66-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 36600-66-5 ]

* 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 [ 36600-66-5 ]

[ 36600-66-5 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 7530-37-2 ]
  • [ 36600-66-5 ]
  • [ 136282-06-9 ]
  • 2
  • [ 36600-66-5 ]
  • [ 83-33-0 ]
  • [ 133587-48-1 ]
  • 3
  • [ 36600-66-5 ]
  • [ 615-13-4 ]
  • [ 136282-05-8 ]
  • [ 136282-19-4 ]
  • 4
  • [ 13865-88-8 ]
  • [ 36600-66-5 ]
  • 10-tert-Butyl-2-methoxy-7H-estra-1,3,4a(14a)-trieno[17,16-b]indole [ No CAS ]
  • 5
  • [ 36600-66-5 ]
  • 3α-Hydroxy-5α-androstan-17-one [ No CAS ]
  • (3R,5S,8S,9S,10S,13S,14S)-17-[(4-tert-Butyl-phenyl)-hydrazono]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol [ No CAS ]
  • 6
  • [ 36600-66-5 ]
  • [ 94-05-3 ]
  • [ 203123-01-7 ]
  • 7
  • [ 648869-31-2 ]
  • [ 326-56-7 ]
  • [ 36600-66-5 ]
  • 3-[5-benzo[1,3]dioxol-5-yl-1-(4-<i>tert</i>-butyl-phenyl)-1<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[5-benzo[1,3]dioxol-5-yl-2-(4-<i>tert</i>-butyl-phenyl)-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 8
  • [ 648869-33-4 ]
  • [ 326-56-7 ]
  • [ 36600-66-5 ]
  • 3-[5-benzo[1,3]dioxol-5-yl-1-(4-<i>tert</i>-butyl-phenyl)-1<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[5-benzo[1,3]dioxol-5-yl-2-(4-<i>tert</i>-butyl-phenyl)-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 9
  • [ 648869-31-2 ]
  • [ 2905-65-9 ]
  • [ 36600-66-5 ]
  • 3-[2-(4-<i>tert</i>-butyl-phenyl)-5-(3-chloro-phenyl)-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[1-(4-<i>tert</i>-butyl-phenyl)-5-(3-chloro-phenyl)-1<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 10
  • [ 648869-33-4 ]
  • [ 2905-65-9 ]
  • [ 36600-66-5 ]
  • 3-[2-(4-<i>tert</i>-butyl-phenyl)-5-(3-chloro-phenyl)-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[1-(4-<i>tert</i>-butyl-phenyl)-5-(3-chloro-phenyl)-1<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 11
  • [ 648869-31-2 ]
  • [ 2459-25-8 ]
  • [ 36600-66-5 ]
  • 3-[2-(4-<i>tert</i>-butyl-phenyl)-5-naphthalen-2-yl-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[1-(4-<i>tert</i>-butyl-phenyl)-5-naphthalen-2-yl-1<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 12
  • [ 648869-33-4 ]
  • [ 2459-25-8 ]
  • [ 36600-66-5 ]
  • 3-[2-(4-<i>tert</i>-butyl-phenyl)-5-naphthalen-2-yl-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[1-(4-<i>tert</i>-butyl-phenyl)-5-naphthalen-2-yl-1<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 13
  • [ 648869-31-2 ]
  • [ 21218-94-0 ]
  • [ 36600-66-5 ]
  • 3-[2-(4-<i>tert</i>-butyl-phenyl)-5-(4-phenoxy-phenyl)-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[1-(4-tert-Butyl-phenyl)-5-(4-phenoxy-phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid [ No CAS ]
  • 14
  • [ 648869-33-4 ]
  • [ 21218-94-0 ]
  • [ 36600-66-5 ]
  • 3-[2-(4-<i>tert</i>-butyl-phenyl)-5-(4-phenoxy-phenyl)-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[1-(4-tert-Butyl-phenyl)-5-(4-phenoxy-phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid [ No CAS ]
  • 15
  • [ 648869-31-2 ]
  • [ 2905-68-2 ]
  • [ 36600-66-5 ]
  • 3-[2-(4-<i>tert</i>-butyl-phenyl)-5-(3,4-dichloro-phenyl)-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[1-(4-<i>tert</i>-butyl-phenyl)-5-(3,4-dichloro-phenyl)-1<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 16
  • [ 648869-33-4 ]
  • [ 2905-68-2 ]
  • [ 36600-66-5 ]
  • 3-[2-(4-<i>tert</i>-butyl-phenyl)-5-(3,4-dichloro-phenyl)-2<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 3-[1-(4-<i>tert</i>-butyl-phenyl)-5-(3,4-dichloro-phenyl)-1<i>H</i>-pyrazol-3-yl]-2-<i>m</i>-tolyl-propionic acid [ No CAS ]
  • 17
  • 6-Hydroxy-1-(3-pyridinyl)-hexan-1,3-dione [ No CAS ]
  • [ 27784-76-5 ]
  • [ 36600-66-5 ]
  • C27H33N3O2 [ No CAS ]
  • C27H33N3O2 [ No CAS ]
  • 18
  • [ 36600-66-5 ]
  • 2-(4-<i>tert</i>-butyl-phenyl)-1-oxy-2,4-dihydro-[1,2,3]triazolo[4,5-<i>d</i>]pyrimidine-5,7-dione [ No CAS ]
  • 19
  • [ 36600-66-5 ]
  • 6-benzoyl-5'-tert-butyl-1'-methyl-3,5-diphenyldispiro[cyclohexa-2,4-diene-1,2'-indoline-3',1"-cyclohexane] [ No CAS ]
  • 20
  • [ 36600-66-5 ]
  • 5'-tert-butyl-1',2'-dimethylspiro[cyclohexane-1,3'-indolium] perchlorate [ No CAS ]
  • 21
  • [ 36600-66-5 ]
  • 2-tert-butyl-10,10-dimethyl-6,8-diphenyl-10H-pyrido[1,2-a]indolium perchlorate [ No CAS ]
  • 22
  • [ 36600-66-5 ]
  • 4-{<i>N</i>'-[3-amino-1-(4-<i>tert</i>-butyl-phenyl)-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-3-hydroxy-naphthalene-1-sulfonic acid [ No CAS ]
  • 23
  • [ 36600-66-5 ]
  • [ 222733-86-0 ]
  • 24
  • [ 36600-66-5 ]
  • 5-(t-butyl)-N-methyltryptamine [ No CAS ]
  • 25
  • [ 36600-66-5 ]
  • [2-(5-<i>tert</i>-butyl-1<i>H</i>-indol-3-yl)-ethyl]-dimethyl-amine [ No CAS ]
  • 26
  • [ 36600-66-5 ]
  • [2-(5-<i>tert</i>-butyl-1<i>H</i>-indol-3-yl)-ethyl]-propyl-amine [ No CAS ]
  • 27
  • [ 36600-66-5 ]
  • tert-butyl 2-(5-tert-butyl-1H-indol-3-yl)ethyl-carbamate [ No CAS ]
  • 28
  • [ 36600-66-5 ]
  • [2-(5-<i>tert</i>-butyl-1<i>H</i>-indol-3-yl)-ethyl]-dipropyl-amine [ No CAS ]
  • 29
  • [ 36600-66-5 ]
  • 7-(4-tert-Butyl-phenyl)-1-methyl-2,2-dioxo-1,2,3,7-tetrahydro-2λ6-pyrazolo[3,4-c][1,2]thiazin-4-one [ No CAS ]
  • 30
  • [ 36600-66-5 ]
  • [ 203123-09-5 ]
  • 31
  • [ 36600-66-5 ]
  • [ 203123-15-3 ]
  • 32
  • [ 36600-66-5 ]
  • [ 203123-03-9 ]
  • 33
  • [ 36600-66-5 ]
  • 2α-Acetoxy-10-tert-butyl-7H-(14α-androstano[17,16-b]indole) [ No CAS ]
  • 34
  • [ 36600-66-5 ]
  • 10-tert-Butyl-6b,11b-dihydro-2-methoxy-7H-estra-1,3,4a(14a)-trieno[17,16-b]indole [ No CAS ]
  • 35
  • [ 36600-66-5 ]
  • anti-2α-Acetoxy-10-tert-butyl-6b,11b-dihydro-7H-(14α-androstano[17,16-b]indole) [ No CAS ]
  • 36
  • [ 36600-66-5 ]
  • [ 133571-85-4 ]
  • 37
  • [ 36600-66-5 ]
  • [ 133571-58-1 ]
  • 38
  • [ 36600-66-5 ]
  • [ 133571-84-3 ]
  • 39
  • [ 36600-66-5 ]
  • Lithium; (4bR,9bS)-8-tert-butyl-9b,10-dihydro-4bH-indeno[1,2-b]indole-5-carboxylate [ No CAS ]
  • 40
  • [ 142314-70-3 ]
  • [ 36600-66-5 ]
  • [ 846055-77-4 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; acetic acid; at 200℃; for 0.333333h;Microwave irradiation; A solution of the aldehyde (Step C, 0.58 g, 3.3 mmol), 4-t-butylphenylhydrazine-HCl (0.66 g, 3.3 mmol), AcOH (1 mL), and dioxane (3 mL) in a sealed reaction vial was heated at 200° C. for 20 min in a microwave. Upon cooling, the residue was diluted with EtOAc (10 mL), then hexane (10 mL). The resulting precipitate was filtered to afford the desired compound as a tan solid. MS m/e 324 (M+H)+. Calc'd for C18H17N3O3- 323.35.
  • 41
  • [ 59997-51-2 ]
  • [ 36600-66-5 ]
  • [ 905589-38-0 ]
YieldReaction ConditionsOperation in experiment
In methanol; ethyl acetate; (1) A solution of pivaloylacetonitrile (4.60 g) and <strong>[36600-66-5]4-tert-butylphenylhydrazine hydrochloride</strong> (3.167 g) in a mixed solvent of ethyl acetate (63 mL) and methanol (7 mL) was heated under reflux for 12 hr. The solvent of the reaction mixture was evaporated, and the residue was poured into ethyl acetate. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried, and the solvent was evaporated. The residue was purified by column chromatography to give 3-tert-butyl-1-(4-tert-butylphenyl)-1H-pyrazol-5-amine (3.54 g). 1H-NMR (300 MHz, CDCl3) deltappm 1.21 (9 H, s) 1.31 (9 H, s) 5.15 (2 H, br s) 5.36 (1 H, s) 7.46 (4 H, m)
  • 42
  • [ 36600-66-5 ]
  • [ 75-36-5 ]
  • [ 76-05-1 ]
  • [ 460746-46-7 ]
  • [ 460748-72-5 ]
YieldReaction ConditionsOperation in experiment
4% With formic acid; tin(IV) chloride; In methanol; dichloromethane; acetonitrile; Example 159 4-(3-acetyl-2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile The product of Example 1D (330 mg, 1.0 mmol) was dissolved into CH2Cl2 (500 muL) and cooled to 0° C. Acetyl chloride (140 muL, 2.0 mmol) and 1 M SnCl4 in CH2Cl2 (1.5 mL, 1.5 mmol) were added, the reaction was permitted to warm to room temperature and it was stirred overnight. The mixture was partitioned between 20percent EtOAc/CH2Cl2 and 0.5 M aqueous dipotassium hydrogen phosphate. The aqueous phase and solids were separated and extracted with CH2Cl2, and the organic phases were combined and worked up as usual but with an aqueous dipotassium hydrogen phosphate wash, dried (Na2SO4), and concentrated. The residue was then resubjected to the same reaction conditions used previously except with additional CH2Cl2 (7 mL), stirred for five days, and worked up as before. The concentrated residue was chromatographed through silica (MeOH/EtOAc/CH2Cl2) to afford an inseparable mixture of product and starting material. The mixture (260 mg) and <strong>[36600-66-5](4-tert-butylphenyl)-hydrazine hydrochloride</strong> (201 mg, 1.0 mmol) were dissolved into methanol (2 mL) and treated with 88percent aqueous formic acid. The mixture was stirred overnight, concentrated, partitioned between 0.5 M dipotassium hydrogen phosphate and CH2Cl2, worked up as usual, dried (Na2SO4), concentrated, and chromatographed through silica with a gradient of 0.5 to 4percent MeOH in 20percent MECN/CH2Cl2. The appropriate fractions were concentrated, and after a few days appeared to have decomposed, partially to the desired ketone. The residue was rechromatographed through a short column of silica with a gradient of 0 to 4percent MeOH/CH2Cl2, and then purified by HPLC [Waters Nova-Pak HR C18 column (40 mm*100 mm, 6 mum particle size) using a gradient of 10percent to 100percent MeCN/0.1percent aqueous TFA over 12 min (15 min run time) at a flow rate of 70 mL/min.] to provide the title compound (4percent yield). MS (ESI APCI) m/z 373 (M+H)+; 1H-NMR (300 MHz, CD3OD) delta 1.49 (d, 3H), 1.68-1.84 (m, 1H), 2.01-2.25 (m, 2H), 2.31-2.46 (m, 1H), 2.80 (s, 3H), 3.3-3.71 (m, 5H), 3.76-3.92 (m, 2H), 7.69-7.76 (m, 2H), 7.84 (d, 2H), 7.89 (d, 2H), 8.20-8.22 (m, 1H).
  • 43
  • N-(3-[1-(4-tert-butylphenyl)-5-pyridin-3-yl-1H-pyrazol-3-yl]propanoyl)tyrosinamide [ No CAS ]
  • [ 36600-66-5 ]
  • N-(3-[1-(4-tert-butylphenyl)-3-pyridin-3-yl-1H-pyrazol-5-yl]propanoyl)tyrosinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; Compound 3-B: 3-{1-(4-tert-butylphenyl)-5-pyridin-3-yl-1H-pyrazol-3-yl}propan-1-ol and 3-{1-(4-tert-butylphenyl)-3-pyridin-3-yl-1H-pyrazol-5-yl}propan-1-ol. A solution of compound 3-A (370 mg, 1.79 mmol) and <strong>[36600-66-5]4-tert-butylphenylhydrazine hydrochloride</strong> (359 mg, 1.79 mmol) in absolute methanol (10 mL) was stirred overnight at 25° C. The reaction mixture was then adsorbed on silica gel (5 g) and purified by flash chromatography on silica gel (60 g), eluding with DCM/MeOH/NH4OH (96/4/1), to afford 709 mg of a yellow oil containing the pyrazole 3-B (two regioisomers, 452 mg, 75percent, ratio 24/76) and DMSO. An aliquot of this mixture was purified with preparative HPLC deltapack C18 column, using a gradient of water/acetonitrile from 95/5 to 50/50 in 60 min, to give pure samples of the two regioisomers. More Polar Regioisomer 1H NMR (CDCl3): delta 8.80 (s, 1H), 8.76 (d, J=5.0 Hz, 1H), 7.95 (d, J=8.1), 7.70 (dd, J=8.1, 5.4 Hz, 1H), 7.43 (d, J=7.7 Hz, 2H), 7.16 (d, J=8.1Hz, 2H),6.60 (s, 1H), 4.48 (t, J=6.0 Hz, 2H), 2.88 (t, J=7.3Hz, 2H), 2.23(pent., J=7.0 Hz, 2H), 1.32 (s, 9H). MS (ESI,+): 336 (M+1)
  • 44
  • [ 36600-66-5 ]
  • [ 128230-98-8 ]
  • [ 128231-13-0 ]
YieldReaction ConditionsOperation in experiment
83% EXAMPLE 24 5-(3,6-Dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl) -1H-indole-2,3-dione 3-[4-(1,1-dimethylethyl) phenylhydrazone] STR45 Starting from 1,3-dihydro-5-(3,6-dihydro-6-methyl-2-oxo -2H-1,3,4-thiadiazin-5-yl)-3-phenylimino-2H-indol-2-one, and 4t-butyl phenylhydrazine hydrochloride and following the method described in Example 21, the desired compound was obtained. Yield: 83percent m.p.: 299° C. IR (KBr): upsilon=3,200; 1,680; 1,635; 1,615; 1,550; 1,180 cm-1. NMR (DMSO-d6): delta=1.29 (s,9H,t-Bu); 1.50(d,J=7.1 Hz,3H, CH3CH); 4.82 (q,J=7.1 Hz,1H,CH3CH); 7.00 (d,J=8.3 Hz,1H, Ar); 7.41 (s,4H,ArtBu); 7.72 (d,J=8.3 Hz,1H,Ar); 7.99 (s,1H,Ar); 11.26 (s,1H,exch.D2 O,NH); 11.66 (s,1H,exch. D2 O,NH); 12.77 (s,1H,exch.D2 O,NH).
  • 45
  • [ 36600-66-5 ]
  • [ 551-93-9 ]
  • [ 917966-92-8 ]
YieldReaction ConditionsOperation in experiment
Example 54; 1-(2-(5-tert-butyl-1H-indol-2-yl)phenyl)-3-(4-(trifluoromethoxy)phenyl)urea; 54a. 2-(5-tert-butyl-1H-indol-2-yl)aniline; 2-aminoacetophenone (1 g, 7.4 mmol), 4-tertbutylphenylhydrazine hydrochloride (1.48g, 7.4 mmol) and acetic acid (0.5 mL) were added to EtOH (25 mL) and refluxed for 30 min. The mixture was evaporated in vacuo. Methanesulfonic acid (17 mL) and phosphorus pentoxide (2.2 g, 15.5 mmol) were added and the mixture was heated at 80° C. for 2 h. The reaction mixture was poured over crushed ice and basified using sodium hydroxide pellets. The solid formed was isolated by filtration, washed with water and air dried to yield the desired material (4.45 g, directly used in the next step without further purification).
  • 46
  • [ 36600-66-5 ]
  • [ 138163-08-3 ]
  • [ 918421-64-4 ]
YieldReaction ConditionsOperation in experiment
51% To a flask under N2 containing 4-^butylphenylhydrazine hydrochloride (1.0 g, 5 mmol) in degassed toluene/CH3CN (50/1, 22 mL) and TFA (1.5 g, 13 mmol) was added 1- ben2yloxycarbonyl-piperidine-4-carbaldehyde (1.2 g, 5 mmol) at room temperature. After stirring for 15 min, the reaction was heated to 400C and stirred overnight. The reaction was cooled to 50C, and MeOH (27 mL) was added and followed by NaBH4 (0.25 g, 6.7 mmol). The reaction was stirred for an additional 1 h, diluted with EtOAc (60 mL), and washed with IN NaOH (2x) and brine. The organic layer was dried with anhydrous MgSO4 and concentrated to afford solid residue, which was washed with hexane/ether (5/1) several times to give 1.0 g (51 percent) of 1'- (benzyloxycarbonyl)- 1 ,2-dihydro-5 -^-buryl-spiro [3H-indole-3 ,4 ' -piperidine] . LC-MS m/z 379 (M + H)+; 1H NMR (400 MHz, DMSO-fe) delta 7.39-7.31 (m, 5 H), 7.01 (s, 1 H), 6.93 (d, 1 H, J= 7.8 Hz), 6.41 (d, 1 H, J= 7.8 Hz), 5.34 (s, 1 H), 5.10 (s, 2 H), 3.98 (bd, 2 H, J= 13 Hz), 3.37 (s, 2 H), 2.98 (bm, 2 H), 1.71-1.55 (m, 4 H), 1.21 (s, 9 H).
  • 47
  • [ 1003869-42-8 ]
  • [ 36600-66-5 ]
  • [ 1003869-43-9 ]
  • 48
  • [ 36600-66-5 ]
  • [ 252894-39-6 ]
  • [ 1003869-22-4 ]
  • 49
  • [ 36600-66-5 ]
  • [ 141-97-9 ]
  • [ 681427-09-8 ]
YieldReaction ConditionsOperation in experiment
78% In acetic acid; at 100℃; for 22h; (1) 1-(4-t-Phenyl)-5-hydroxy-3-methyl-1H-pyrazole 4-t-Butylphenylhydrazine hydrochloride (24.2 g, 120 mmol) in acetic acid (600 mL) was stirred with ethyl acetoacetate (16.4 mL, 129 mmol) at 100°C for 22 hours. The solvent was removed by distillation under reduced pressure, and the resulting solid was recrystallized from chloroform (70 ml, 40°C)-diethyl ether (200 mL, 0°C), washed with diethyl ether and dried under reduced pressure to give 21.7 g of the desired product (78percent yield). Morphology: colorless solid LC/MS: Condition 2, retention time 3.52 (min) LC/MS (ESI+) m/z; 231 [M+1]
69% With acetic acid; at 110℃; for 6h; Example 2; Preparation of 4-[2-(3-cyclohexyl-2-hydroxyphenyl)hydrazin-1-ylidene]-1-(4-tert-butylphenyl)-3-methyl-4,5-dihydro-]H-pyrazol-5-one; Step 1:; Compound 2a (1-<strong>[36600-66-5][4-(tert-butyl)phenyl]hydrazine hydrochloride</strong>, Maybridge Catalog Number BTB08670EA) (2.0 g, 10.0 mmol) and ethyl acetoacetate (1.95 g, 15.0 mmol) were heated in acetic acid (20 mL) to reflux at an oil bath temperature of 110 deg C. for 6 hours. The amber solution was allowed to cool, and the solvent was removed under reduced pressure. The residue was suspended in 40percent ethyl acetate-hexanes (25 mL) and allowed to stir for 1 h. The resulting precipitate was filtered and washed with 40percent ethyl acetate-hexanes to afford Compound 2b as a white powder (1.58 g, 69percent) (i.e., Example compound 4(a) in PCT International Patent Publication No. WO2001/089457 A2, herein incorporated by reference in its entirety).
  • 50
  • [ 1203608-45-0 ]
  • [ 36600-66-5 ]
  • 5-(2-bromophenyl)-1-(4-tert-butyl-phenyl)-1H-pyrazole [ No CAS ]
  • 51
  • [ 1203608-46-1 ]
  • [ 36600-66-5 ]
  • [ 1203608-53-0 ]
  • 52
  • [ 532-24-1 ]
  • [ 36600-66-5 ]
  • [ 1220278-98-7 ]
YieldReaction ConditionsOperation in experiment
A suspension of (4-ter.pound.-butylphenyl)hydrazine hydrochloride (1000 mg, 5.0 mmol;Aldrich), tropinone (696 mg, 5.0 mmol; Aldrich), and 4 M HCl-dioxane (2.5 mL, 10.0 mmol; Aldrich) in ethanol (10 mL) was heated to 80 °C for 16 hours. After cooling to room temperature, the reaction mixture was concentrated, basified with 5 NNaOH (aqueous), and then extracted with ethyl acetate (3x50 mL). The combined organic phase was concentrated and the residue was purified by reverse-phase HPLC [Waters XBridge.(TM). RP 18 column, 5 mum, 30x100 mm, flow rate 40 mL/minute, 20-95percent gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (300 MHz, methanol-^) delta ppm 1.36 (s, 9 H), 1.61 - 1.74 (m, 1 H), 1.93 (t, J=9 Hz, 1 H), 2.25 - 2.36 (m, 2 H), 2.41 (s, 3 H), 2.48 (d, J=17 Hz, 1 H), 3.21 - 3.29 (m, 1 H), 3.56 - 3.63 (m, 1 H), 4.26 (d, J=4 Hz, 1 H), 7.10 - 7.15 (m, 1 H), 7.16 - 7.21 (m, 1 H), 7.38 (d, J=I Hz, 1 H); MS (DCI/NH3) m/z 269 (M+H)+.
  • 53
  • [ 85302-07-4 ]
  • [ 36600-66-5 ]
  • [ 1203661-42-0 ]
  • 54
  • [ 36600-66-5 ]
  • [ 34737-83-2 ]
  • 8-tert-butoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 15A [0419] (4-te/t-Butylphenyl)hydrazine hydrochloride (I g, 4.98 mmol) was dissolved in 7percent H2SO4 in 1,4-dioxane (50 mL), l-methylpiperidin-4-1 hydrochloride (0.742 g, 4.98 mmol) was added and stirred at 80 0C for 3 h. Reaction was monitored by TLC LCMS. After completion of the reaction, reaction mixture was concentrated under vacuum and quenched with aq. NaHCO3 solution, extracted with EtOAc. Organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum and purified by column chromatography (5percent Methanol- DCM) to afford 0.51 g of 8-tert-butoxy-2-methyl-2,3,4,5-tetrahydro-lH-pyrido[4,3-b]indole. 1H NMR (DMSO-J6, free base) d (ppm) 11.1 (bs,lH), 10.6 (bs, IH), 7.4 (s, IH), 7.3-7.2 (d,lH), 7.2-7.1 (d, IH), 4.6-4.5 (m, IH), 4.3 (bs, IH), 3.7 (bs, IH), 3.5 (bs, IH), 3.2-3.3 (m, 2H), 2.9 (s, 3H),1.3 (s, 9H).
  • 55
  • [ 36600-66-5 ]
  • [ 94-02-0 ]
  • [ 1257976-34-3 ]
  • 56
  • [ 39755-95-8 ]
  • [ 36600-66-5 ]
  • [ 1263428-98-3 ]
YieldReaction ConditionsOperation in experiment
77% In methanol; at 20℃; General procedure: Suitable indoline-2,3-dione 1a-c (1.0 mmol) was dissolved in methanol (5 mL) with gentle heating, then arylhydrazine (2.4 mmol) was slowly added with stirring at room temperature. After stirring overnight, the resulting precipitate was filtered and crystallized or the reaction mixture was evaporated to dryness and the residue suitably purified.
  • 57
  • [ 1445-73-4 ]
  • [ 36600-66-5 ]
  • [ 1147938-68-8 ]
  • 58
  • [ 36600-66-5 ]
  • [ 1354547-24-2 ]
  • 59
  • [ 36600-66-5 ]
  • [ 1354547-12-8 ]
  • 60
  • [ 21352-99-8 ]
  • [ 36600-66-5 ]
  • [ 1409944-83-7 ]
  • 61
  • [ 1422045-46-2 ]
  • [ 36600-66-5 ]
  • [ 1422045-58-6 ]
  • 62
  • [ 1003909-32-7 ]
  • [ 36600-66-5 ]
  • [ 1422045-54-2 ]
  • 63
  • C24H29NO6 [ No CAS ]
  • [ 36600-66-5 ]
  • C27H35N3O5 [ No CAS ]
  • 64
  • [ 36600-66-5 ]
  • [ 94-41-7 ]
  • [ 161055-61-4 ]
  • 65
  • [ 36600-66-5 ]
  • [ 94-41-7 ]
  • [ 161055-61-4 ]
  • [ 1456823-43-0 ]
  • 66
  • [ 36600-66-5 ]
  • [ 94-41-7 ]
  • [ 1456823-43-0 ]
  • 67
  • [ 21551-47-3 ]
  • [ 36600-66-5 ]
  • [ 1456823-38-3 ]
  • 68
  • [ 21551-47-3 ]
  • [ 36600-66-5 ]
  • [ 1456823-49-6 ]
  • 69
  • [ 1221963-20-7 ]
  • [ 36600-66-5 ]
  • [ 1456823-39-4 ]
  • 70
  • [ 1221963-20-7 ]
  • [ 36600-66-5 ]
  • [ 1456823-50-9 ]
  • 71
  • [ 6552-62-1 ]
  • [ 36600-66-5 ]
  • [ 1456823-41-8 ]
  • 72
  • [ 6552-62-1 ]
  • [ 36600-66-5 ]
  • [ 1456823-52-1 ]
  • 73
  • [ 36600-66-5 ]
  • [ 908303-07-1 ]
  • C26H31NO4 [ No CAS ]
  • 74
  • [ 36600-66-5 ]
  • [ 65-85-0 ]
  • N'-(4-(tert-butyl)phenyl)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); triethylamine; In N,N-dimethyl-formamide; at 20℃; General procedure: To a solution of benzoic acid (610.6mg, 5mmol) and phenylhydrazine hydrochloride (723.0mg, 5mmol) in DMF (10.0mL) was added HCTU (5-Chloro-1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate) (2275.3mg, 5.5mmol) and Et3N (2085.0mL, 15mmol). The reaction mixture was stirred at room temperature for overnight. Then the reaction mixture was washed with saturated NH4Cl (aq), NaHCO3 (aq) and brine. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography to give 1a as a white solid (955.2mg, 90percent).
  • 75
  • [ 2960-66-9 ]
  • [ 36600-66-5 ]
  • 5-(1,1-dimethylethyl)-1H-indole-3-acetic acid ethyl ester [ No CAS ]
  • 76
  • [ 2960-66-9 ]
  • [ 36600-66-5 ]
  • (2E,4E)-4-{2-[4-(1,1-dimethylethyl)phenyl]hydrazono}-2-butenoic acid ethyl ester [ No CAS ]
  • 77
  • [ 36600-66-5 ]
  • [ 3788-94-1 ]
  • [ 1225558-43-9 ]
YieldReaction ConditionsOperation in experiment
4.5 g Journal of Chemical Society Perkin Trans I (J. Chem. Soc. Perkin trans. Of I), p. 1875 (ethoxy-methylene-up gave the synthesized 2-to the method described in 1988), ethyl acetoacetate (13.92g) in ethanol (4-tert- butyl phenyl hydrazine in 45) hydrochloride solution (15.0g) adding an aqueous solution (45), and stirred for 4 hours at reflux temperature. After adding water to the reaction liquid, extracted with ethyl acetate, washed with saturated aqueous sodium chloride, and distilled to remove the solvent under reduced pressure. To the residue sodium hydroxide (5.9g), water (45), addition of ethanol (45), and stirred for 2 hours at reflux temperature. After the reaction, the solvent was distilled off, and washed with toluene, and then remove the acidic by addition of dilute hydrochloric acid to the aqueous layer, after extraction with ethyl acetate, dried over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure. By overriding the precipitated solid with ethyl acetate / n- hexane solvents to obtain the title compound (4.50g).
  • 78
  • [ 34846-90-7 ]
  • [ 36600-66-5 ]
  • 1-(4-tertbutylphenyl)-5-hydroxypyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.1% In methanol; for 6h;Reflux; To three reaction vials, 20. lg (100 mmol) of <strong>[36600-66-5]4-tert-butylphenylhydrazine hydrochloride</strong>, 11.6 g (100 mmol) of methyl methacrylate, and 1.0 mL of methanol were added. The reaction mixture was heated to reflux for about 6 hours. The reaction solution was quantified by liquid chromatography, and 1- (4-tertButylphenyl) -5-hydroxypyrazole in a yield of 84.1percent.
  • 79
  • [ 201230-82-2 ]
  • [ 19820-56-5 ]
  • [ 36600-66-5 ]
  • 2-(4-(tert-butyl)phenyl)phthalazin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With palladium(II) trifluoroacetate; 1,3-bis-(diphenylphosphino)propane; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 150℃; under 7500.75 Torr; for 21h;Autoclave; General procedure: 2-Formylaryl tosylate (2 mmol), hydrazine (2 mmol), Pd(TFA)2 (5 molpercent), dppp (10 molpercent), DBU (2.4 mmol), anhydrous MgSO4 (2 mmol) and CH3CN (30 ml) were charged in a 200 ml-autoclave. The autoclave was flushed using CO three times. The reaction was pressurized with CO to 1.0 MPa, and stirred at 140 °C for 21 h. Then the mixture was cooled to room temperature and the excess CO was vented. Solvent was removed under reduced pressure and the crude residue was purified by column chromatography on silica gel with petroleum ether-ethyl acetate as the eluent to afford the desired product.
  • 80
  • [ 110-91-8 ]
  • [ 201230-82-2 ]
  • [ 36600-66-5 ]
  • [ 79868-24-9 ]
YieldReaction ConditionsOperation in experiment
90% With oxygen; palladium diacetate; sodium carbonate; triphenylphosphine; In 1,4-dioxane; dimethylsulfoxide-d6; carbon dioxide; at 100℃; for 12h;Schlenk technique; liquid CO2; To a clean 25 mL Schlenk tube was added 0.4 mmol of <strong>[36600-66-5]4-tert-butylphenylhydrazine hydrochloride</strong> andPd (OAc) 3 (1.3 mg, 3 molpercent), PPh3 (10.5 mg, 20 molpercent), Na2CO3 (21.2 mg, 0.2 mmol)In CO: O2 = 3: 1(17.4 mg, 0.2 mmol) and a mixed solvent(Dmso: dioxane = 0.1: 0.9mL), reaction at 100 for 12h, TLC plate detection;Of morpholine (& lt; RTI ID = 0.0 & gt;2) After completion of the reaction, the reaction solution was added with 2 mL of water and extracted with EA for 3-5 times. The organic layer was concentrated and purifiedColumn chromatography afforded the pure amide compound as a yellow solid in 90percent yield.
  • 81
  • [ 201230-82-2 ]
  • [ 36600-66-5 ]
  • [ 108-95-2 ]
  • [ 26459-51-8 ]
  • 82
  • [ 36600-66-5 ]
  • [ 98-53-3 ]
  • 3,6-di-tert-butyl-2,3,4,9-tetrahydro-1H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With hydrogenchloride; In ethanol; water; for 5h;Reflux; 9-(2-dicyclohexylphosphonophenyl) -3,6-di-tert-butyl-9H-carbazole as shown,The preparation of 9- (2-dicyclohexylphosphonophenyl) -3,6-di-tert-butyl-9H-carbazole is:In a 250 ml round bottom flask,10.0 g of <strong>[36600-66-5]4-tert-butylphenylhydrazine hydrochloride</strong> (60 mmol) was added,Then 8.48 g of 4-tert-butylcyclohexanone (66 mmol) was added,Add 100 ml of ethanol,And then slowly add 5 ml of hydrochloric acid,The mixture was stirred for 5 hours under reflux,After the reaction is completely returned to room temperature,After crystallization, water was collected and washed with water to obtain 14.4 g of 3,6-di-tert-butyl-2,3,4,9-tetrahydro-1H-carbazole,Decompress all the solution,Yield 85percent, can be directly into the next step reaction.
  • 83
  • [ 201230-82-2 ]
  • [ 36600-66-5 ]
  • [ 536-74-3 ]
  • 1,5-bis(4-(tert-butyl)phenyl)-3-phenyl-1H-pyrazole [ No CAS ]
  • 84
  • [ 870-50-8 ]
  • [ 35634-10-7 ]
  • [ 36600-66-5 ]
  • di-tert-butyl 1-(3-(4-(tert-butyl)phenyl)bicyclo[1.1.1]pentan-1-yl)hydrazine-1,2-dicarboxylate [ No CAS ]
  • 85
  • [ 36600-66-5 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • [ 1625-92-9 ]
  • 86
  • [ 696-63-9 ]
  • [ 36600-66-5 ]
  • (4-(tert-butyl)phenyl)(4-methoxyphenyl)sulfane [ No CAS ]
  • 87
  • [ 33439-27-9 ]
  • [ 36600-66-5 ]
  • 8‐(tert‐butyl)‐2‐tosyl‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole [ No CAS ]
  • 88
  • [ 1203549-59-0 ]
  • [ 36600-66-5 ]
  • 3β-acetoxy-17β-[5'-hydroxy-1'-(4"-tert-butylphenyl)-1'H-pyrazol-3'-yl]androst-5-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium acetate; acetic acid; In ethanol; at 120℃; for 0.166667h;Microwave irradiation; General procedure: Arylhydrazine hydrochloride (5d?j, 1.0 mmol) and NaOAc (82 mg, 1.0 mmol) were dissolved in EtOH (10 mL). The reaction mixture was stirred at 40 °C for 10 min and then compound 4 (333 mg, 0.80 mmol) dissolved in AcOH (20 mL) was added. The reaction mixture was irradiated at 120 °C for a given time (max. power: 150 W) and then poured into cold water (10 mL). The resulting precipitate was filtered and the crude product purified by column chromatography
  • 89
  • [ 36600-66-5 ]
  • 4-[2-(3-cyclohexyl-2-hydroxyphenyl)hydrazin-1-ylidene]-1-(4-tert-butylphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-5-one [ No CAS ]
  • 90
  • [ 3972-65-4 ]
  • [ 36600-66-5 ]
  • 91
  • [ 36600-66-5 ]
  • C26H26Br2N2 [ No CAS ]
  • 92
  • [ 36600-66-5 ]
  • C40H34N4S2 [ No CAS ]
  • 93
  • [ 36600-66-5 ]
  • C40H32B2F4N4S2 [ No CAS ]
  • 94
  • [ 36600-66-5 ]
  • C64H52B2N4S2 [ No CAS ]
  • 95
  • [ 36600-66-5 ]
  • [ 637-88-7 ]
  • 2,8-di-tert-butyl-5,11-dihydroindolo[3,2-b]carbazole [ No CAS ]
  • 96
  • [ 36600-66-5 ]
  • [ 108-94-1 ]
  • 9-(tert-butyl)-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid [ No CAS ]
  • 97
  • [ 36600-66-5 ]
  • [ 108-94-1 ]
  • [ 25365-91-7 ]
  • 98
  • 2-(3-carbamoyl-2,4-difluorophenoxy)acetic acid [ No CAS ]
  • [ 36600-66-5 ]
  • 2,6-difluoro-3-((4-(4-(tert-butyl)phenyl)-5-oxo-1,3,4-oxadiazol-2-yl)methoxy)benzamide [ No CAS ]
  • 99
  • 2-(3-carbamoyl-2,4-difluorophenoxy)acetic acid [ No CAS ]
  • [ 36600-66-5 ]
  • C19H21F2N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A 10 mL round-bottom flask equipped with a magnetic stirrer was charged with 7 or 13 (0.26 mmol), EDCI (55 mg, 0.29 mmol), HOBt(39 mg, 0.29 mmol) and THF (5 mL), DMF (1 mL), this mixture wasstirred at room temperature for 3 h. Then the intermediate 10 (0.4 mmol) and followed DIPEA (155 mg, 1.2 mmol) were added to the reaction, and stirred overnight. The mixture was then diluted withEtOAc (30 mL), washed with NH4Cl (aq) and brine, dried over Na2SO4,concentrated in a rotovapor, and purified on silica gel. Elution withDCM/MeOH (30:1) afforded the according products 11 or 14 in goodyield. Example 11-A12, 1H NMR (600 MHz, DMSO-d6) delta 10.04 (s, 1H),8.14 (s, 1H), 8.00 (s, 1H), 7.86 (s, 1H), 7.21-7.14 (m, 3H), 7.13-7.08(m, 1H), 6.71 (d, J=6.8 Hz, 2H), 4.75 (s, 2H). ESI-MS calcd forC15H13ClF2N3O3 [M+H]+, 356.1, found 356.3.The above acylhydrazine intermediate 11 or 14 was dissolved inTHF (5 mL), and triphosgene (2 eq) was added, the mixture was stirredat room temperature for 1 h. Upon completion, the reaction mixturewas then diluted with EtOAc (25 mL), washed with brine, dried overNa2SO4, concentrated in vacuum, and purified on silica gel. Elutionwith petroleum ether/EtOAc (2:1 to 1:1) afforded the according productsin good yield.
  • 100
  • ethyl 4-(3-carbamoyl-2,4-difluorophenoxy)-3-oxobutanoate [ No CAS ]
  • [ 36600-66-5 ]
  • 2,6-difluoro-3-((1-(4-(tert-butyl)phenyl)-5-oxo-4,5-dihydro-1Hpyrazol-3-yl)methoxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 75℃; for 5h; General procedure: A solution of intermediate 29 (50 mg, 0.166 mmol) in 3 mL of EtOH was added the corresponding substituted phenylhydrazine hydrochloride(0.166 mmol), and the mixture was heated at 75 C for 5 h. the resulting solution was concentrated and purified by silica gel with DCM/MeOH (gradient from 150:1 to 60:1) getting the desired compoundsin a yield about 30%.
  • 101
  • 3-(3-carbamoyl-2,4-difluorophenoxy)propanoic acid [ No CAS ]
  • [ 36600-66-5 ]
  • C20H23F2N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A 10 mL round-bottom flask equipped with a magnetic stirrer was charged with 7 or 13 (0.26 mmol), EDCI (55 mg, 0.29 mmol), HOBt(39 mg, 0.29 mmol) and THF (5 mL), DMF (1 mL), this mixture wasstirred at room temperature for 3 h. Then the intermediate 10 (0.4 mmol) and followed DIPEA (155 mg, 1.2 mmol) were added to the reaction, and stirred overnight. The mixture was then diluted withEtOAc (30 mL), washed with NH4Cl (aq) and brine, dried over Na2SO4,concentrated in a rotovapor, and purified on silica gel. Elution withDCM/MeOH (30:1) afforded the according products 11 or 14 in goodyield. Example 11-A12, 1H NMR (600 MHz, DMSO-d6) delta 10.04 (s, 1H),8.14 (s, 1H), 8.00 (s, 1H), 7.86 (s, 1H), 7.21-7.14 (m, 3H), 7.13-7.08(m, 1H), 6.71 (d, J=6.8 Hz, 2H), 4.75 (s, 2H). ESI-MS calcd forC15H13ClF2N3O3 [M+H]+, 356.1, found 356.3.The above acylhydrazine intermediate 11 or 14 was dissolved inTHF (5 mL), and triphosgene (2 eq) was added, the mixture was stirredat room temperature for 1 h. Upon completion, the reaction mixturewas then diluted with EtOAc (25 mL), washed with brine, dried overNa2SO4, concentrated in vacuum, and purified on silica gel. Elutionwith petroleum ether/EtOAc (2:1 to 1:1) afforded the according productsin good yield.
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