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[ CAS No. 886500-93-2 ]

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Chemical Structure| 886500-93-2
Chemical Structure| 886500-93-2
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Product Details of [ 886500-93-2 ]

CAS No. :886500-93-2 MDL No. :MFCD06660249
Formula : C8H5BrClF3O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :289.48 g/mol Pubchem ID :17750697
Synonyms :

Safety of [ 886500-93-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P301+P330+P331-P305+P351+P338-P310-P303+P361+P353 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 886500-93-2 ]

  • Downstream synthetic route of [ 886500-93-2 ]

[ 886500-93-2 ] Synthesis Path-Downstream   1~14

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  • [ 141-97-9 ]
  • [ 1065082-60-1 ]
YieldReaction ConditionsOperation in experiment
INTERMEDIATE 40; Ethyl 2- [4-chloro-3-(trifluoromethoxy)benzyl] -3-oxobutanoate; NaH (0.19 g, 4.8 mmol) was weighed into a large Stem-block tube and washed with dry hexane (25 mL). Dry THF (15 mL) was added and the suspension cooled on an ice-bath. Ethyl 3-oxobutanoate (0.52 g, 4.0 mmol) was added slowly under hydrogen evolution and the reaction mixture allowed to stir for a few minutes until a clear solution was obtained. 4- (Bromomethyl)-l-chloro-2-(trifluoromethoxy)benzene (1.16 g, 4.00 mmol) was added and the reaction mixture heated at 65 0C for 1 h. The reaction mixture was poured on sat. NH4Cl (100 mL) and EtOAc (100 mL), shaked and the phases allowed to separate. The aqueous phase was extracted with EtOAc (2x75 mL), the combined organic phases dried <n="85"/>(Na2SU4) and concentrated to give the title compound as a clear oil which was directly used in the following step.
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YieldReaction ConditionsOperation in experiment
61% INTERMEDIATE 4; Dimethyl [4-chloro-3-(trifluoromethoxy)benzyl] malonate; Sodium hydride (264 mg, 6.60 mmol, 60% in mineral oil) was suspended in dry THF (20 mL) and cooled on an ice-bath. Dimethyl malonate (0.79 g, 6.0 mmol) was added <n="44"/>dropwise under hydrogen evolution and the reaction mixture left to stir for 30 min. 4-(Bromomethyl)-l-chloro-2-(trifluoromethoxy)benzene (0.82 g, 3.0 mmol) was added and the mixture stirred on the thawing ice-bath overnight. The reaction mixture was worked up by pouring on IM HCl (100 mL) and diethyl ether (100 mL). Shaking, separating, washing with sat NH4Cl, drying of the organic phase (Na2SO4), filtration and evaporation gave the crude product as a clear oil containing excess dimethyl malonate. The oil was put under a gentle nitrogen flow overnight at rt, which removed dimethyl malonate effectively to give the title compound (0.73 g, 61%). The crude product was used in following reaction steps without purification.
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  • [ 916210-69-0 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; In water; dimethyl sulfoxide; for 0.5h; 28% Ammonium hydroxide (3.0 mL, 22 mmol NH3) was added to a solution of 4- (bromomethyl)-l-chloro-2-(trifluoromethoxy)benzene (300 mg, 1.04 mmol) and DMSO (4 mL). The reaction was sealed, stirred vigorously for 30 min, vented, poured into EtOAc (40 mL), and then washed with 10% K2CO3 (100 mL x 2). Each aqueous wash was extracted with EtOAc (40 mL). The combined organic extracts were dried, <n="85"/>filtered, and concentrated to give impure (4-chloro-3-(trifluoromethoxy)phenyl)methanamine as a colorless oil. LCMS: 226.1 (M+H)+.
  • 5
  • [ 886500-93-2 ]
  • [ 1417421-60-3 ]
  • [ 1417420-80-4 ]
YieldReaction ConditionsOperation in experiment
30% Example 41. Synthesis of compound 227. Anhydrous dimethylformamide (1 mL) was placed in a 40 mL vial with stir bar and cooled in a metal reaction block in the refrigerator. A solution of J-096 (80 mg, 0.38 mmol, 1.00 equiv) in anhydrous dimethylformamide (2 mL) was placed in a vial and cooled in the refrigerator. (4-Chloro-3-trifluoromethoxy)benzylbromide (143 mg, 0.50 mmol, 1.3 equiv) was dissolved in anhydrous dimethylformamide (1 mL) and cooled in the refrigerator. NaH (12 mg, 0.50 mmol, 1.3 equiv) was added to the cold 40 mL vial via a glass pipette. The contents were swirled and the alcohol solution was added via pipette. The suspension was swirled again and the reaction block returned to the refrigerator. After 30 minutes, the block was removed, the bromide solution added via pipette and the reaction block placed at ambient temperature on a stir plate 16 hrs. Water was added (4 mL) to quench the reaction. The product was extracted into EtOAc and concentrated under reduced pressure.Heptanes (1 mL) and acetonitrile/methanol (3 mL (1 : 1)) were added and shook and the methanolic layer removed and shot onto the chromeleon HPLC (UV detector, MeOH/H20, method: 607-28). Concentration of the desired peaks resulted in the desired product (compound 227, 47 mg, 30%).LC-MS-227: (ES, m/z): 414 [M+H]+ 1H-NMR-227: (400 MHz, CDC13, ppm): delta 8.49(m, 1H), 8.17(dd, J=8 and 0.6, 1H), 8.08(b, 1H), 7.80(dd, J=8 and 2.1, 1H), 7.43(d, J=8.2, 1H), 7.31(s, 1H), 7.21(m, 1H), 4.61(s, 2H), 4.55(s, 2H), 3.28(t, J=6.5 x 2, 2H), 1.89(m, 1H), 0.96(d, J= 6.6, 6H).
  • 6
  • [ 886500-93-2 ]
  • [4-({(1R,3R,4S)-3-(hydroxymethyl)-4-[(triisopropylsilyl)oxy]cyclopentyl}amino)pyrimidin-5-yl](1H-pyrazol-3-yl)methanone [ No CAS ]
  • [(1R,2S,4R)-4-[5-({1-[4-chloro-3-(trifluoromethoxy)benzyl]-1H-pyrazol-3-yl}carbonyl)pyrimidin-4-yl]amino}-2-hydroxycyclopentyl]methyl sulfamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Step 2: [(lR,2S,4R)-4-[5-({l-[4-Chloro-3-(trifluoromethoxy)benzyl]-lH-pyrazol-3- yl}carbonyl)pyrimidin-4-yl] amino}-2-hydroxycyclopentyl]methyl sulfamate 1-152 To a 50 mL reaction vial was added [4-({(lR,3R,4S)-3-(hydroxymethyl)-4- [(triisopropylsilyl)oxy] cyclopentyl}amino)pyrimidin-5-yl](lH-pyrazol-3-yl)methanone (0.14 g, 0.31 mmol), 4-chloro-3-(trifluoromethoxy)benzylbromide (0.11 g, 0.39 mmol), cesium carbonate (0.41 g, 1.25 mmol), and THF (4.0 mL). The mixture was stirred at rt for 2 h. To the vial was added brine (1 mL), water (1 mL) and EtOAc (20 mL). After separation, the aqueous layer was extracted with EtOAc (5 mL). The combined organic phases were concentrated. To the vial was then added chlorosulfonamide (0.15 g, 1.25 mmol), TEA (0.17 mL, 1.25 mmol), and acetonitrile (2 mL). After the reaction stirred at rt for 1 h, saturated NaHC03 (2 mL) and EtOAc (20 mL) were added. After separation of the phases, the aqueous layer was extracted with EtOAc (5 mL). The combined organic phases were then concentrated. To the resulting solid in the reaction vial was added TFA (5.0 mL) and water (0.5 mL). After this mixture was stirred at rt for 16 h, solvent was completely evaporated. This residue was dissolved in MeOH (10 mL) and to it was added MP PL-C03 resin (3 g). After this mixture was stirred at rt for 2 h, the resin was filtered and rinsed with MeOH (10 mL). The filtrate was then evaporated and the resulting residue was purified by prep-HPLC to give [(lR,2S,4R)-4-[5-({l-[4-chloro-3-(trifluoromethoxy)benzyl]-lH-pyrazol- 3-yl}carbonyl)pyrimidin-4-yl]amino}-2-hydroxycyclopentyl]methyl sulfamate (0.122 g, 66%). 'H NMR (MeOD) 5 9.61 (s, 1H), 8.57 (s, lH), 7.88 (d, J= 2.4 Hz, 1H), 7.59 (d, J= 8.4 Hz, 1H), 7.38 (s, 1H), 7.30 (d, J= 8.4, 1H), 6.98 (s, 1H), 5.53 (s, 2H), 4.82 (m, 1H), 4.21 (m, 3H), 2.55 (m, 1H), 2.31 (m, 1H), 2.17 (m, 1H), 1.92 (m, 1H), 1.45 (m, 1H). LCMS (FA): m/z = 592 (M+H).
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  • 14
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  • [ 1065080-60-5 ]
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