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[ CAS No. 850012-44-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 850012-44-1
Chemical Structure| 850012-44-1
Chemical Structure| 850012-44-1
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Product Details of [ 850012-44-1 ]

CAS No. :850012-44-1 MDL No. :MFCD09965991
Formula : C10H14BrN Boiling Point : -
Linear Structure Formula :- InChI Key :MRHVSOBPZBXNEB-UHFFFAOYSA-N
M.W : 228.13 Pubchem ID :11959000
Synonyms :

Calculated chemistry of [ 850012-44-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.82
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.48
Log Po/w (XLOGP3) : 3.6
Log Po/w (WLOGP) : 3.34
Log Po/w (MLOGP) : 3.46
Log Po/w (SILICOS-IT) : 2.93
Consensus Log Po/w : 3.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.83
Solubility : 0.034 mg/ml ; 0.000149 mol/l
Class : Soluble
Log S (Ali) : -3.83
Solubility : 0.0335 mg/ml ; 0.000147 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.11
Solubility : 0.0178 mg/ml ; 0.000078 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.45

Safety of [ 850012-44-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 850012-44-1 ]

* 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 [ 850012-44-1 ]

[ 850012-44-1 ] Synthesis Path-Downstream   1~96

  • 2
  • [ 6310-21-0 ]
  • [ 850012-44-1 ]
YieldReaction ConditionsOperation in experiment
100% With tetra-N-butylammonium tribromide; In tetrahydrofuran; at 0 - 20℃; for 0.166667h; 25 g of 2 ferf-butylaniline (168 mmol) are dissolved in 250 mL of THF; the reaction mixture is stirred and cooled to O0C, and 81 g of tetrabutylammonium bromide (TBA-Br3) (168 mmol) are then added portionwise while maintaining the temperature between 00C and 5C. The temperature is then allowed to rise to about room temperature and the mixture is stirred for 10 minutes. The reaction is stopped by adding 250 mL of water and is then extracted with 250 mL of ethyl acetate. The organic phases are washed with 1 L of saturated Na2S2O5 solution and EPO <DP n="21"/>then dried over magnesium sulfate. The solvents are evaporated off and the residue is filtered through a pad of silica (pure heptane, then a 3/7 heptane/ethyl acetate mixture). 43.6 g of 4-bromo-2-te/?-butylaniline (yield = 100%) are obtained in the form of a white solid.
100% With tetra-N-butylammonium tribromide; In tetrahydrofuran; at 5℃; for 1.25h;Product distribution / selectivity; Example 703-(1-[6-cyclopropyl-4-(1,1-dimethylethyl)-1-methyl-1H-benzimidazopiperidinyl)-1,3-oxazolidin-2-oneStep A[4-bromo-2-( 1, 1-dimethylethyl)phenyl]amine[00330] To a solution of 2-tert-butylaniline (52.2 mL, 335 mmol) in THF (618 mL) at 5 C (ice-water bath) was added tetrabutylammonium tribromide (146 g, 303 mmol) in THF (200 mL) dropwise over 45 minutes. After 30 minutes, the mixture was quenched with water (100 mL) and stirred for 15 minutes. The mixture was diluted with diethyl ether (1 L) and washed with saturated aqueous NaHC03 (400 mL), then brine (400 mL), dried (Na2S04), filtered and concentrated to give [4-bromo-2-(1 ,1-dimethylethyl)phenyl]amine (78.40 g, 344 mmol, quantitative yield) as brown oil. This was used for next step. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.30 (s, 9 H), 4.98 (s, 2 H), 6.57 - 6.62 (m, 1 H), 7.02 (dd, J=8.5, 2.3 Hz, 1 H), 7.09 (d, J=2.3 Hz, 1 H); MS(ESI) m/z: 228.1 , 230.2 (MH+).
98% With tetrabuthylammonium tribromide; In tetrahydrofuran; at 0℃; for 0.5h; Reference Example 8 4-Bromo-2-tert-butylaniline To a solution of 2-tert-butylaniline (50 g, 335 mmol) in THF (500 mL) was added tetrabutylammonium tribromide (234.5 g, 335 mmol) at 0 C. After the solution was stirred for 30 minutes at that temperature, it was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated Na2S2O3 solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=100:0 to 20:80) to provide 4-bromo-2-tert-butylaniline (74.6 g, 98%) as a pink oil. 1H NMR (300 MHz, CDCl3) delta 1.39 (s, 9H), 3.81 (br. s., 2H), 6.51 (d, J=8.3 Hz, 1H), 7.11 (dd, J=8.3, 2.3 Hz, 1H), 7.30 (d, J=2.3 Hz, 1H).
83% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 1h;Product distribution / selectivity; Step 1 : 4-Bromo-2-(tert-butyl)aniline (P25a)To a solution of 2-ferf-butylaniline (14.9 g, 100 mmol) was added a solution of NBS (17.8 g, 100 mmol) in DMF at rt. The reaction mixture was stirred for 1 h at rt, diluted with water (30 mL) and extracted with Et20 (3 x 250 mL). The organic layer was washed with brine, dried over Na2S0 , concentrated and purified by CC to give compound P25a (19 g, 83%).
83% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; Step 1 : 4-Bromo-2-(tert-butvuaniline (P38a) To a solution of 2-(tert-butyl)aniline (14.9 g, 100 mmol) was added a solution of NBS (17.8 g, 100 mmol) in DMF at rt. The mixture was stirred overnight at rt, diluted with water (30 mL) and extracted with Et20 (3x 250 mL). The organic layer was washed with brine, dried over Na2S04, concentrated and purified by CC to give compound P38a (19 g, 83%).
79% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 4h; Step 1: 4-Bromo-2-tert-butylaniline (19a) To a solution of NBS (218 mg, 1 mmol) in DMF was added a solution of 2-tert-butylaniline (149 mg, 1 mmol) in DMF at rt. The reaction mixture was stirred for 4 h at rt. After the reaction was completed (monitored by LC-MS), water (30 mL) was added and the reaction mixture was extracted with EA (150 mL). The organic layer was washed with brine and dried over Na2SO4, concentrated in vacuo and purified by CC (hexane/EA = 3:1) to give the title compound 19a (180 mg, 79%).
79% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 4h; Step 1: 4-Bromo-2-tert-butylaniline (Pla) To a solution of NBS (218 mg, 1 mmol) in DMF was added a solution of 2-tert-butylaniline(149 mg, 1 mmol) in DMF at rt. The reaction mixture was stirred for 4 h at ii, then water (30mL) was added and the mixture was extracted with EA (150 mL). The organic layer waswashed with brine and dried over Na2SO4, concentrated and purified by CC (hexane/EA = 3/1)to give compound Pla (180 mg, 79%).
79% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 4h; Step 1 : 4-Bromo-2-ferf-butylaniline (P1a) To a solution of NBS (218 mg, 1 mmol) in DMF was added a solution of 2-tert-butylaniline (149 mg, 1 mmol) in DMF at rt. The reaction mixture was stirred for 4 h at rt, then water (30 mL) was added and the mixture was extracted with EA (150 mL). The organic layer was washed with brine and dried over Na2S04, concentrated and purified by CC (hexane/EA = 3/1) to give compound P1a ( 80 mg, 79%).
79% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 2h; To a solution of 2-tert-butyl- (10 mL, 67 mmol) in DMF (130 mL) was added N-bromosuccinimide (6.9 g, 80 mmol). The reaction was stirred at rt for 2 h and then partitioned between water and EtOAc. The aqueous phase was washed with additional EtOAc and the organic phases were combined, washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: 10-100% EtOAc/heptane) to provide 4-bromo-2-(tert-butyl)aniline (12 g, 53 mmol, 79% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.10 (d, J=2.5 Hz, 1H), 7.03 (dd, J=8.5, 2.3 Hz, 1H), 6.61 (d, J=8.5 Hz, 1H), 4.97 (s, 2H), 1.31 (s, 9H). m/z (ESI, +ve ion): 229.8 (M+H)+.
71% Example 1; Synthesis of 4-[2-(3-tert-Butyl-4-diethylaminophenyl)-2-hydroxyiminoethoxy]benzoic acid:; a. Preparation of 4-Bromo-2-tert-butylaniline:; 51.8 g (347 mmol) of 2-tert-butylaniline (commercial product marketed especially by the company Aldrich) are dissolved in 600 ml of glacial acetic acid. 900 ml of aqueous 48% hydrobromic acid are then added, and the reaction medium is then cooled to 0 C. 300 ml of DMSO are then added dropwise, after which the reaction medium is warmed to room temperature. After stirring for 4 hours, 250 ml of ethyl acetate are added, followed by 400 ml of 5N sodium hydroxide, and then 1.75 l of 10N sodium hydroxide, to bring the pH to 8. 250 ml of ethyl acetate are added and the medium is separated by settling of the phases. The aqueous phase is then re-extracted with 500 ml of ethyl acetate. The combined organic phases are then rinsed with 1 l of water, and then concentrated under reduced pressure. The residue obtained is purified by chromatography (eluent: 95/5 heptane/ethyl acetate). An orange-colored oil is obtained (m=56.2 g, yield=71%).
65% 25 g (168 mmol) of 2-tert-butylaniline are placed in 300 ml of acetic acid. 450 ml of aqueous HBr at 48% are added and the mixture is then cooled to 0 C. 150 ml of DMSO are added dropwise, the mixture having been brought back to ambient temperature is stirred for 2 hours and it is then poured into ice-cold water and basified to pH 10 with 5N NaOH. It is extracted with diethyl ether and the organic phase is then dried and concentrated to dryness. The residue is column-purified (95/5 heptane/EtOAc). 25.2 g of 4-bromo-2-tert-butylphenylamine are obtained in the form of a yellow oil (yield=65%).
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; To a solution of 2-t-butylaniline (45 g, 0.3 mol, 1 eq) in DMF (250 mL) was added NBS (53.6 g, 0.3 mmol, 1 eq) portionwise at 0 oC. The mixture was stirred at rt overnight, TLC indicated completion. The reaction was poured into ice-water (500 mL), extracted with EA (200 mL x 3). The combined organic layers were washed with brine (200 mLx3), dried over sodium sulfate, concentrated affording 4-bromo-2-t-butylaniline (75 g, crude, containing DMF) which was used in next step directly. 1HNMR (300 MHz, CDCl3): G 7.32 (s, 1 H), 7.14- 7.11 (d, J = 10.5 Hz, 1 H), 6.53 (d, J = 8.4 Hz, 1 H), 3.74 (br, 2 H), 1.41 (s, 9 H).^

Reference: [1]Patent: WO2006/66978,2006,A1 .Location in patent: Page/Page column 19-20
[2]Patent: WO2011/97491,2011,A1 .Location in patent: Page/Page column 126-127
[3]Patent: US2012/71489,2012,A1 .Location in patent: Page/Page column 56
[4]Patent: WO2012/139775,2012,A1 .Location in patent: Page/Page column 53
[5]Patent: WO2013/79223,2013,A1 .Location in patent: Page/Page column 83
[6]Patent: EP2511263,2012,A1 .Location in patent: Page/Page column 42
[7]Patent: WO2013/178362,2013,A1 .Location in patent: Page/Page column 92
[8]Patent: WO2014/23367,2014,A1 .Location in patent: Page/Page column 64
[9]Patent: US2019/345169,2019,A1 .Location in patent: Paragraph 0255; 0256
[10]Tetrahedron Letters,2010,vol. 51,p. 3116 - 3118
[11]Patent: US2007/4726,2007,A1 .Location in patent: Page/Page column 6
[12]Patent: US2010/261754,2010,A1 .Location in patent: Page/Page column 4
[13]Angewandte Chemie - International Edition,2017,vol. 56,p. 10582 - 10586
    Angew. Chem.,2017,vol. 129,p. 10718 - 10722,5
[14]Journal of the American Chemical Society,2012,vol. 134,p. 7262 - 7265
[15]Journal of the American Chemical Society,2017,vol. 139,p. 1714 - 1717
[16]Mutation Research - Genetic Toxicology and Environmental Mutagenesis,2000,vol. 467,p. 55 - 68
[17]Journal of Organic Chemistry,2006,vol. 71,p. 4786 - 4794
[18]Angewandte Chemie - International Edition,2016,vol. 55,p. 9084 - 9087
    Angew. Chem.,2016,vol. 128,p. 9230 - 9233,4
[19]Patent: WO2017/120429,2017,A1 .Location in patent: Page/Page column 284
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  • [ 850012-44-1 ]
  • [ 126747-14-6 ]
  • [ 899215-68-0 ]
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  • [ 850012-44-1 ]
  • [ 149104-90-5 ]
  • [ 899215-67-9 ]
  • 6
  • [ 108-31-6 ]
  • [ 850012-44-1 ]
  • 1-(4-bromo-2-(tert-butyl)phenyl)-1H-pyrrole-2,5-dione [ No CAS ]
  • 7
  • [ 850012-44-1 ]
  • C20H20BrNO2 [ No CAS ]
  • 8
  • [ 850012-44-1 ]
  • C20H20BrNO2 [ No CAS ]
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  • [ 850012-44-1 ]
  • [ 899215-70-4 ]
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  • [ 850012-44-1 ]
  • [ 899215-69-1 ]
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  • [ 899215-74-8 ]
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  • [ 899215-72-6 ]
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  • [ 899215-73-7 ]
  • 14
  • [ 850012-44-1 ]
  • [ 899215-71-5 ]
  • 15
  • [ 850012-44-1 ]
  • N-[2-(methoxycarbonyl)-2-propoxy]-2-phenyl-4-(cyanophenyl)-6-tert-butylphenylaminyl [ No CAS ]
  • 16
  • [ 850012-44-1 ]
  • N-[2-(methoxycarbonyl)-2-propoxy]-2-phenyl-4-(acetylphenyl)-6-tert-butylphenylaminyl [ No CAS ]
  • 17
  • [ 850012-44-1 ]
  • N-(2-cyano-4-methyl-2-pentoxy)-2-phenyl-4-(cyanophenyl)-6-tert-butylphenylaminyl [ No CAS ]
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  • [ 850012-44-1 ]
  • 3-<i>tert</i>-butyl-4-nitroso-biphenyl [ No CAS ]
  • 21
  • [ 850012-44-1 ]
  • [ 4635-59-0 ]
  • [ 895543-24-5 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine; In dichloromethane; at 0 - 20℃; for 1.5h; 20 g (0.0877 mol; 1 eq.) of <strong>[850012-44-1]2-tert-butyl-4-bromoaniline</strong> (prepared according to Example 1 a)) are dissolved in 100 ml of dichloromethane at about O0C.13 ml (0.0921 mol; 1.05 eq.) of triethylamine are added, followed, after 15 minutes, by addition of 10.5 ml (0.0921 mol; 1.05 eq.) of 4-chlorobutanoyl chloride.At the end of the addition, the reaction medium is returned to room temperature and stirred for 1 hour 30 minutes. 70 ml of H2O are added and the reaction medium is then allowed to settle. The aqueous phase is re-extracted with dichloromethane, and the organic phases are collected and washed successively with aqueous 1M NaHCtheta3 and then with H2O.The resulting organic phase is dried over sodium sulfate, filtered and concentrated on a rotavapor. EPO <DP n="71"/>An orange crystalline powder (m = 31 g) is obtained, which, after recristallization from heptane/ethyl acetate medium, gives 24 g of N-(2-tert-butyl-4-bromophenyl)-4- chlorobutanamide (yield = 82%).
YieldReaction ConditionsOperation in experiment
Examples of p-brominated o-alkylanilines corresponding to this formula include: ... 4-bromo-2-ethylaniline 4-bromo-2-propylaniline 4-bromo-2-isopropylaniline 4-bromo-2-n-butylaniline 4-bromo-2-t-butylaniline 4-bromo-2-sec-butylaniline 4-bromo-2-isobutylaniline 4-bromo-2-n-pentylaniline ...
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  • [ 850012-44-1 ]
  • [ 1219832-04-8 ]
YieldReaction ConditionsOperation in experiment
55% With iodine; In ethanol; Example 18N-{(S)-1-[7-tert-Butyl-1-methyl-5-(2-oxo-1,2-dihydro-pyridin-3-yl)-1H-indole-3-carbonyl]-pyrrolidin-3-ylmethyl}-methanesulfonamide (I-111) step 1-To a solution of 80a (12.0 g, 52.6 mmol, CASRN 850012-44-1) in EtOH (150 mL) was added iodine (14.7 g, 57.8 mmol). When the iodine dissolved Ag2SO4 (18.0 g, 57.8 mmol) was added and the reaction stirred for 1.5 h at RT. The solid silver salts were removed by filtration and washed with EtOH. The filtrate was concentrated and redissolved in DCM, washed sequentially with 10% aq. Na2S2O3 and water, dried (MgSO4), filtered and concentrated. The crude product was purified by SiO2 chromatography eluting with a DCM/hexane gradient (0 to 20% DCM) to afford 10.3 g (55%) of 80b.
90 g A mixture of <strong>[850012-44-1]4-bromo-2-t-butylaniline</strong> (70 g, 0.3 mol, 1 eq) and I2 (78 g, 0.3 mol, 1 eq) in cyclohexane (350 mL) was heated to 50 oC for 30 minutes, after the mixture was clear, 30% H2O2 (25 g, 0.3 mol, 1 eq) was added dropwise. And then the mixture was stirred at this temperature for 4 hours. After cooling down to rt, the mixture was diluted with EA (500 mL), washed with aqueous (300 mL x 3) and brine (300 mL x 3), dried over sodium sulfate, concentrated and purified by silica column affording 4-bromo-2-t-butyl-6-iodoaniline (90 g, 83%). 1HNMR (300 MHz, CDCl3): G 7.70 (s, 1 H), 7.31 (s, 1 H), 1.41 (s, 9 H).
  • 24
  • [ 850012-44-1 ]
  • [ 1079742-66-7 ]
YieldReaction ConditionsOperation in experiment
99% With N-chloro-succinimide; In N,N-dimethyl-formamide; at 70℃; for 2h; 6.4 g (48 mmol) of N-chlorosuccinimide are added to a solution of 10 g (44 mmol) of 4-bromo-2-tert-butylphenylamine (example 1a) in 150 ml of DMF. The medium is heated at 70 C. for 2 hours. It is then poured into a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic phases are combined and washed with water and then dried over sodium sulphate. The residue is chromatographed on silica gel (90/10 heptane/ethyl acetate). 11.4 g of 4-bromo-2-tert-butyl-6-chlorophenylamine are obtained in the form of an orange oil (yield=99%).
With N-chloro-succinimide; In dichloromethane; acetonitrile; at 20 - 80℃; Step B[00252] 4-bromo-2-(1 ,1-dimethylethyl)aniline (3.4 g, 15 mmol) was dissolved in dichloromethane (100 mL) and N-chlorosuccinimide (2.0 g, 15 mmol) added portion-wise. The mixture was stirred for 3 hours at room temperature. 3Acetonitrile (100 mL) was added and the reaction flask heated in an oil bath at 80 C. No reflux condenser was added so that the dichloromethane could slowly evaporate. The internal temperature reached about 65 C and a reflux condenser was attached. The mixture was heated for 2 more hours. An additional 1 g of N-chlorosuccinimide was added slowly portion-wise at temperature and the mixture continued to heat overnight. The reaction was allowed to cool to room temperature and was concentrated to 75 mL of solvent. Brine was added and the mixture extracted 2 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica chromatography eluting with 35% dichloromethane in hexanes. Fractions were concentrated to give the title compound (3.13 g, 65% purity, 52%) as a redish oil.
  • 25
  • [ 850012-44-1 ]
  • [ 75-03-6 ]
  • [ 895542-86-6 ]
YieldReaction ConditionsOperation in experiment
65% 2.7 g (68 mmol) of sodium hydride are suspended in 250 ml of DMSO, under a stream of nitrogen. 7 g (31 mmol) of 4-bromo-2-tert-butylphenylamine, diluted in 10 ml of DMSO, are added to the reaction medium cooled to 0 C. After stirring at ambient temperature for 30 minutes, 5.4 ml (68 mmol) of ethyl iodide are added slowly. The pale-yellow-coloured mixture is stirred overnight at ambient temperature and then poured into a saturated solution of ammonium chloride and extracted twice with ethyl acetate. The organic phase is dried and then concentrated under vacuum. 5 g of (4-bromo-2-tert-butylphenyl)ethylamine are obtained in the form of a yellow oil (yield=65%).
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  • [ 850012-44-1 ]
  • [ 75-03-6 ]
  • [ 850012-45-2 ]
YieldReaction ConditionsOperation in experiment
67% b. Preparation of (4-Bromo-2-tert-butylphenyl)diethylamine: 20 g (88 mmol) of <strong>[850012-44-1]4-bromo-2-tert-butylaniline</strong> are dissolved in 200 ml of DMSO under a nitrogen atmosphere. 7.7 g (190 mmol) of sodium hydride are added portionwise. After stirring for 30 minutes, 15.4 ml (190 mmol) of ethyl iodide are added dropwise. The reaction medium is stirred for 12 hours and then poured into saturated ammonium chloride solution. After extraction with ethyl acetate, the reaction sequence is repeated, and the residue is then purified by chromatography on a column of silica (eluent: 98/2 heptane/ethyl acetate). A colorless oil is obtained (m=16.7 g, yield=67%).
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  • [ 1352342-40-5 ]
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  • [ 1370513-60-2 ]
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  • [ 1352342-42-7 ]
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  • [ 1352342-43-8 ]
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  • [ 1352338-47-6 ]
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  • [ 1352342-44-9 ]
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  • [ 850012-44-1 ]
  • [ 762-21-0 ]
  • [ 1352342-39-2 ]
YieldReaction ConditionsOperation in experiment
4-Bromo-2-trifluoromethyl-phenylamine (72.9 g, 0.32 mol) and But-2-ynedioic acid diethyl ester (59.9 g, 0.353 mol) were dissolved in MeOH (120ml) in a 500 ml round bottom flask and refluxed for 2h. The volatiles were removed in vacuo, and the residue was placed in a pre-heated reaction block (220C) and fitted with a vacuum adapter and a thermocouple (J-KEM). The reaction was heated under house vacuum (~ 80 torr) until the internal temperature reached 187C (~ 45 min). Analysis by LCMS indicates the reaction was complete. The reaction was allowed to cool in air with vigorous stirring using an overhead stirrer. Once the reaction had cooled to 120C, heptane was added portionwise, providing a thick slurry of crystalline product. The slurry was stirred at reflux for one hour, then cooled to rt and stirred overnight. Filtration provided the desired compound C (81.1 g, 72 % Yield) and a tan powder. MS [M+H]+ = 352.23 (100%), 354.0 (90%).
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  • [ 850012-44-1 ]
  • [ 821-48-7 ]
  • 1-(4-bromo-2-tert-butylphenyl)piperazine dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% Reference Example 9 1-(4-Bromo-2-tert-butylphenyl)piperazine dihydrochloride A suspension of <strong>[850012-44-1]4-bromo-2-tert-butylaniline</strong> (Reference Example 8, 25.0 g, 110 mmol) and bis(2-chloroethyl)amine hydrochloride (21.5 g, 120 mmol) in diethylene glycol dimethyl ether (157 mL) was stirred for 3 days at 170 C. It was cooled to room temperature, added 1 M sodium hydroxide solution (50 mL), and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crude product. It was diluted with ethyl acetate and ether (50:50) and added 1 M hydrochloric acid solution to provide 1-(4-bromo-2-tert-butylphenyl)piperazine dihydrochloride (16.2 g, 40%) as a gray solid. 1H NMR (300 MHz, DMSO-d6) delta 1.37 (s, 9H), 2.81 (d, J=11.7 Hz, 2H), 2.87-3.09 (m, 2H), 3.09-3.21 (m, 2H), 3.33 (d, J=11.7 Hz, 2H), 7.27 (d, J=8.7 Hz, 1H), 7.42 (d, J=2.3 Hz, 1H), 7.49 (dd, J=8.3, 2.3 Hz, 1H), 9.50 (br. s., 2H).
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  • [ 1373752-23-8 ]
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  • [ 20442-98-2 ]
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  • [ 1373752-24-9 ]
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  • [ 1373751-85-9 ]
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  • [ 1373751-86-0 ]
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  • [ 1373751-88-2 ]
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  • [ 850012-44-1 ]
  • [ 1373751-92-8 ]
  • 45
  • [ 850012-44-1 ]
  • [ 1373751-93-9 ]
  • 47
  • [ 850012-44-1 ]
  • [ 1373751-95-1 ]
  • 50
  • [ 850012-44-1 ]
  • [ 544-97-8 ]
  • [ 2909-81-1 ]
  • 51
  • [ 850012-44-1 ]
  • [ 192182-54-0 ]
  • [ 1373752-25-0 ]
  • 53
  • [ 850012-44-1 ]
  • [ 1326310-69-3 ]
  • 54
  • [ 850012-44-1 ]
  • [ 1326310-70-6 ]
  • 55
  • [ 850012-44-1 ]
  • [ 1326310-71-7 ]
  • 56
  • [ 850012-44-1 ]
  • [ 1326310-72-8 ]
  • 57
  • [ 850012-44-1 ]
  • 4-[6-bromo-4-(1,1-dimethylethyl)-1-methyl-1H-benzimidazol-2-yl]carbonyl}-1-(trans-4-hydroxycyclohexyl)-2-piperazinone [ No CAS ]
  • 58
  • [ 850012-44-1 ]
  • 4-[6-cyclopropyl-4-(1,1-dimethylethyl)-1-methyl-1H-benzimidazol-2-yl]carbonyl}-1-(trans-4-hydroxycyclohexyl)-2-piperazinone [ No CAS ]
  • 59
  • [ 850012-44-1 ]
  • 6-bromo-4-(1,1-dimethylethyl)-1-methyl-1H-benzimidazole-2-carboxylate [ No CAS ]
  • 60
  • [ 850012-44-1 ]
  • [ 1402890-11-2 ]
YieldReaction ConditionsOperation in experiment
45% Step 2: 4-Bromo-2-tert-butylbenzene-1-sulfonylchloride (19b) 4-Bromo-2-tert-butylaniline 19a (20 mmol) was added to a mixture of conc. HCl (11.2 mL) and glacial acetic acid (2.24 mL) at -10C. To this mixture, a solution of NaNO2 (1.518 g, 22 mmol) in minimum amount of water was added dropwise at -10C. After stirring for 45 minutes at -10C the diazonium salt solution was obtained. SO2 gas was bubbled into glacial acetic acid (22.4 mL) in a three-neck flask until saturation (30 min). Then CuCl (0.49 g, 0.49 mmol) was added and stirring was continued until the mixture turned green. The flask was placed in an ice bath and the diazonium salt solution was added droppwise at 5C. After the addition was complete, the mixture was stirred overnight at rt and poured into ice water. The solid was collected by filtration to give the title compound 19b (45% yield).
45% Step 2: 4-Bromo-2-fert-butylbenzene-1-sulfonyl chloride (PI 9b)4-Bromo-2-?e/i-butylaniline P19a (20 mmol) was added to a mixture of cone. HCI (1 1.2 mL) and AcOH (2.24 mL) at -10C. To this mixture, a solution of NaN02 (1.52 g, 22 mmol) in minimum amount of water was added dropwise at -10C. After stirring for 45 min at -10C the diazonium salt solution was obtained. S02 gas was bubbled into AcOH (22.4 mL) in a three-neck flask until saturation (30 min). Then CuCI (0.49 g, 0.49 mmol) was added and stirring was continued until the mixture turned green. The flask was placed in an ice bath and the diazonium salt solution was added dropwise at 5C. After the addition was complete, the mixture was stirred overnight at rt and poured into ice water. The solid was collected by filtration to give the compound P19b (45%).
45% Step 2: 4-Bromo-2- tert-butylbenzene- 1 -sulfonyl chloride (P1 b)4-Bromo-2-tert-butylaniline Pla (20 mmcl) was added to a mixture of conG. HCI (11.2 mL) andAcOH (2.24 mL) at -10C. To this mixture, a solution of NaNO2 (1.52 g, 22 mmcl) in minimumamount of water was added dropwise at -10C. After stirring for 45 mm at -10C thediazonium salt solution was obtained. SO2 gas was bubbled into AcOH (22.4 mL) in a three- neck flask until saturation (30 mm). Then CuCI (0.49 g, 0.49 mmol) was added and stirring was continued until the mixture turned green. The flask was placed in an ice bath and the diazonium salt solution was added dropwise at 5C. After the addition was complete, themixture was stirred overnight at rt and poured into ice water. The solid was collected by filtration to give the compound P1 b (45%).
45% Step 2: 4-Bromo-2-ferf-butylbenzene-1-sulfonyl chloride (P1 b) 4-Bromo-2-terf-butylaniline P1a (20 mmol) was added to a mixture of cone. HCI (11.2 mL) and AcOH (2.24 mL) at -10C. To this mixture, a solution of NaN02 (1.52 g, 22 mmol) in minimum amount of water was added dropwise at -10C. After stirring for 45 min at -10C the diazonium salt solution was obtained. S02 gas was bubbled into AcOH (22.4 mL) in a three-neck flask until saturation (30 min). Then CuCI (0.49 g, 0.49 mmol) was added and stirring was continued until the mixture turned green. The flask was placed in an ice bath and the diazonium salt solution was added dropwise at 5C. After the addition was complete, the mixture was stirred overnight at rt and poured into ice water. The solid was collected by filtration to give the compound P1b (45%).

  • 63
  • [ 850012-44-1 ]
  • [ 1402889-15-9 ]
  • 64
  • [ 850012-44-1 ]
  • [ 111-44-4 ]
  • [ 1403387-39-2 ]
YieldReaction ConditionsOperation in experiment
15% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 120℃; for 1h;Microwave irradiation; Step 2: 4-(4-Bromo-2-(tert-butyl)phenyl)morpholine (P25b) To a microwave vial (20 mL) equipped with a magnetic bar was added compound P25a (1.0 g, 4.4 mmol), 1-chloro-2-(2-chloroethoxy)ethane (1.1 g, 7.6 mmol), Kl (2.2 g, 13.2 mmol) and K2C03 (1.2 g, 8.8 mmol) in DMF. The mixture was stirred under microwave irradiation at 120C for 1 h, cooled, poured into water (20 mL) and extracted with Et20 (3 x 25 mL). The combined organic layers were dried over Na2S04, evaporated and purified by CC to afford compound P25b (200 mg, 15%).
  • 65
  • [ 850012-44-1 ]
  • [ 1403387-03-0 ]
  • 66
  • [ 850012-44-1 ]
  • [ 1403387-00-7 ]
  • 67
  • [ 850012-44-1 ]
  • [ 1403387-01-8 ]
  • 68
  • [ 850012-44-1 ]
  • [ 1403387-38-1 ]
  • 69
  • [ 850012-44-1 ]
  • [ 1403387-42-7 ]
  • 70
  • [ 850012-44-1 ]
  • [ 1403387-40-5 ]
  • 71
  • [ 850012-44-1 ]
  • [ 1403384-20-2 ]
  • 72
  • [ 850012-44-1 ]
  • [ 1403384-22-4 ]
  • 73
  • [ 111-24-0 ]
  • [ 850012-44-1 ]
  • [ 1079742-60-1 ]
YieldReaction ConditionsOperation in experiment
19% Step 1 : 1-(4-Bromo-2-(fert-butyl)phenyl)piperidine (P27a)To a solution of NaH (72 mg, 3.0 mmol) in dry DMF was added P25a (228 mg, 1.0 mmol) and the mixture was stirred at 25C for 0.5 h. Then 1 ,5-dibromopentane was added dropwise and the mixture was stirred at 80C for 40 h, cooled, poured into water (20 mL) and extracted with Et20 (3 x 25 mL). The combined organic layers were dried over Na2S04, evaporated and purified by CC to afford compound P27a (50 mg, 19%) as yellow oil.
  • 74
  • [ 3350-78-5 ]
  • [ 850012-44-1 ]
  • [ 1403387-02-9 ]
YieldReaction ConditionsOperation in experiment
48% In toluene; Step 2: /V-(4-Bromo-2-(tert-butvnphenyl)-3-methylbut-2-enamide (P13b)A mixture of compound P13a (2.3 g, 10 mmol) and 3-methylbut-2-enoyl chloride (1.4 g, 12 mmol) in toluene (20 mL) was stirred overnight, quenched with water and extracted with EA (3 x 50 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered, concentrated and purified by CC to give P13b (1.5 g, 48%) as a white solid.
  • 75
  • [ 39229-33-9 ]
  • [ 850012-44-1 ]
  • [ 1403387-41-6 ]
YieldReaction ConditionsOperation in experiment
64% In toluene; at 110℃; for 1.5h; Step 1 : /N/-(4-Bromo-2-(ferf-butyl)phenyl)-2-(2-chloroethoxy)acetamide (P26a)A mixture of compound P25a (2.28 g, 10 mmol) and 2-(2-chloroethoxy)acetyl chloride (1.57 g, 10 mmol) in toluene was heated at 110C for 1.5 h, concentrated, diluted with water (100 mL) and extracted with EA. The combined organic layers were washed with brine, dried over Na2S04, concentrated and purified by CC to give compound P26a (2.3 g, 64%).
  • 76
  • [ 850012-44-1 ]
  • [ 75-87-6 ]
  • [ 1442431-10-8 ]
YieldReaction ConditionsOperation in experiment
5 g With hydrogenchloride; hydroxylamine hydrochloride; In water; at 55℃; for 18h;Inert atmosphere; Step 2: /V-(4-Bromo-2-(fert-butyl)phenyl)-2-(hvdroxyimino)acetamide (P38b) To a solution of compound P38a (5.0 g, 21.9 mmol), hydroxylamine hydrochloride (5.48 g, 78.9 mmol) and sodium sulfate (24.9 g, 175 mmol) in H20 (150 mL) and 2M HCI (7.4 mL) at rt under N2 was added chloral hydrate (3.88 g, 26.3 mmol). The resulting solution was stirred at 55C for 18 h, cooled to rt, diluted with water (100 mL) and extracted with EA (3x 50 mL). The combined organic layers were concentrated to give P38b (5 g) as a viscous oil.
  • 77
  • [ 850012-44-1 ]
  • [ 1442431-11-9 ]
  • 78
  • [ 850012-44-1 ]
  • [ 1442431-12-0 ]
  • 79
  • [ 850012-44-1 ]
  • ethyl 5-(3-(tert-butyl)-4-(N-(tert-butyl)sulfamoyl)phenyl)-4-(cyclohexyl(methoxy)methyl)thiazole-2-carboxylate [ No CAS ]
  • 80
  • [ 850012-44-1 ]
  • potassium 5-(3-(tert-butyl)-4-(N-(tert-butyl)sulfamoyl)phenyl)-4-(cyclohexyl(methoxy)methyl)thiazole-2-carboxylate [ No CAS ]
  • 81
  • [ 850012-44-1 ]
  • trans-methyl 3-(5-(3-(tert-butyl)-4-(N-(tert-butyl)sulfamoyl)phenyl)-4-(cyclohexyl(methoxy)methyl)thiazole-2-carboxamido)cyclobutanecarboxylate [ No CAS ]
  • 82
  • [ 850012-44-1 ]
  • trans-3-(5-(3-(tert-butyl)-4-(N-(tert-butyl)sulfamoyl)phenyl)-4-(cyclohexyl(methoxy)methyl)thiazole-2-carboxamido)cyclobutanecarboxylic acid [ No CAS ]
  • 83
  • [ 850012-44-1 ]
  • [ 98-80-6 ]
  • 3-(2-methyl-1-phenylpropan-2-yl)-[1,1’-biphenyl]-4-amine [ No CAS ]
  • 85
  • [ 850012-44-1 ]
  • [ 66003-76-7 ]
  • 4-bromo-2-(2-methyl-1-phenylpropan-2-yl)aniline [ No CAS ]
  • 4-bromo-2-(2-methyl-1,3-diphenylpropan-2-yl)aniline [ No CAS ]
  • 86
  • methyl 2-acetyl-4-(3-bromophenyl)-4-oxobutanoate [ No CAS ]
  • [ 850012-44-1 ]
  • methyl 1-(4-bromo-2-(tert-butyl)phenyl)-5-(3-bromophenyl)-2-methyl-1H-pyrrole-3-carboxylate [ No CAS ]
  • 87
  • methyl 2-acetyl-4-(3-bromophenyl)-4-oxobutanoate [ No CAS ]
  • [ 850012-44-1 ]
  • (R)-methyl 1-(4-bromo-2-(tert-butyl)phenyl)-5-(3-bromophenyl)-2-methyl-1H-pyrrole-3-carboxylate [ No CAS ]
  • 95
  • [ 850012-44-1 ]
  • copper(l) cyanide [ No CAS ]
  • 2-tert-butyl-4-cyanoaniline [ No CAS ]
  • 96
  • [ 850012-44-1 ]
  • N-(5-(4-(7-t-butyl-1H-indol-3-yl)pyrimidin-2-ylamino)-2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxyphenyl)acrylamide [ No CAS ]
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