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[ CAS No. 111628-39-8 ] {[proInfo.proName]}

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Chemical Structure| 111628-39-8
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Product Details of [ 111628-39-8 ]

CAS No. :111628-39-8 MDL No. :MFCD04035522
Formula : C11H13N3O Boiling Point : -
Linear Structure Formula :- InChI Key :HLKHIJZYKGDCJM-UHFFFAOYSA-N
M.W : 203.24 Pubchem ID :647818
Synonyms :

Safety of [ 111628-39-8 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 111628-39-8 ]

* 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 [ 111628-39-8 ]

[ 111628-39-8 ] Synthesis Path-Downstream   1~65

  • 1
  • [ 110-85-0 ]
  • [ 615-18-9 ]
  • [ 111628-39-8 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; In dichloromethane; water; at 0℃; for 0.5h; 5.6g (65 mmol) Piperazine (water free) and 3.27g (0.325 mol) triethylamine was dissolved in 50 ml of dry CH2Cl2 and the solution cooled to 0C in an ice/salt bath. 2-Chlorobenzoxazole (4d) dissolved in 20 ml of dry CH2Cl2 was added dropwise to the solution under stirring keeping the solution at 0C. After the addition, the mixture was stirred for a further 30 min at 0C and then quenched with 200 ml of ice-water. After separation of the organic phase, the water phase was extracted with ethyl acetate (2 x 100 ml), the combined organic phases was washed with sat. NaCl solution, dried over anhyd. Na2SO4, filtered and evaporated to dryness. Compound 8d was isolated as a white solid over column chromatography using silica gel with CH2Cl2/MeOH (5:1) as eluent. Yield 4.96 g (75%). 1HNMR (δ ppm): 3.48-3.53 (m, 4H, PZI); 3.17 (s, 1H, NH); 2.75-2.80 (m, 4H, PZI); 6.99 (dt, J=1.6Hz, J=8Hz, 1H, BZO-H5); 7.18 (dt, J=1.2Hz, J=7.6Hz, 1H, BZO-H6); 7.27 (dd, J=1.4Hz, J=7.6Hz, 1H, BZO-H7); 7.37 (dd, J=0.6Hz, J=7.8Hz, 1H, BZO-H4).
75% With triethylamine; In dichloromethane; at 0℃; 5.6g (65 mM) Piperazine (water free) and3.27g (0.325 mol) triethylamine was dissolved in 50 ml of dry CH2Cl2 and the solution cooledto 0C in an ice/salt bath. 2-Chlorobenzoxazole (1c) dissolved in 20 mL of dry CH2Cl2 wasadded dropwise to the solution under stirring keeping the solution at 0C. After the addition,the mixture was stirred for a further 30 min at 0C and then quenched with 200 mL of icewater.After separation of the organic phase, the water phase was extracted with ethyl acetate(2 x 100 mL), the combined organic phases was washed with sat. NaCl solution, dried overanhyd. Na2SO4, filtered and evaporated to dryness. Compound 8d was isolated as a white solidover column chromatography using silica gel with CH2Cl2/MeOH (5:1) as eluent. Yield 4.96 g(75%). 1H NMR (200 MHz, d6-DMSO, d): 3.48-3.53 (m, 4H, 4x Pip-H); 3.17 (s, 1H, NH);2.75-2.80 (m, 4H, 4x Pip-H); 6.99 (dt, J = 1.6Hz, J = 8Hz, 1H, BZO-H5); 7.18 (dt, J = 1.2Hz,J = 7.6Hz, 1H, BZO-H6); 7.27 (dd, J = 1.4Hz, J = 7.6Hz, 1H, BZO-H7); 7.37 (dd, J = 0.6Hz,J = 7.8Hz, 1H, BZO-H4).
72% In N,N-dimethyl-formamide; at 90℃; for 3h;Inert atmosphere; A solution of piperazine (0.7 g, 8.2 mmol, 2.5 eq.) and 2-chlorobenzoxazole (0.5 g, 3.27 mmol) in dry DMF (10 mL) was stirred at 90 C for 3 hours under inert conditions. After the mixture was allowed to cool down, water (10mL) was added and the mixture was acidified to pH 2 with concentrated HCI prior to be washed with DCM (2X20 mL). The aqueous phase was adjusted to pH 12 with NaOH 4N and extracted with DCM (3X25 mL). The organic phase was washed with water (4X10 mL), dried over MgS04 and concentrated under reduced pressure to afford 2-piperazin-1 -yl-1 ,3-benzoxazole (0.48 g, 72%). ESI-MS m/z: 204 ([M+H]+ , 100%); RT= 0.9 min(Method 3).
55% With triethylamine; In dichloromethane; at 0℃; for 0.5h; Step l 0.90 g (10.4 mmol) of piperazine was dissolved in 50 ml of dichloromethane in a dried round flask provided with nitrogen gas, 0.80 g (5.2 mmol) of 2-chlorobenzooxazole and 0.9 ml (52.1 mmol) of triethylamine were added thereto at 0C , and the mixture was incubated at 0C for 30 mins. After adding water thereto, the reaction mixture was extracted with ethyl acetate, and the formed organic layer was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting residue was subjected to silica gel column chromatography (dichloromethane:methanol=9:l) to obtain 0.58 g of 2-(piperazin-l-yl)benzooxazole (yield: 55%).
With triethylamine; In dichloromethane; water; INVENTIVE EXAMPLE 14 2-(1-Piperazinyl)benzoxazole Anhydrous piperazine (5.6 g) was dissolved in methylene chloride (100 ml) to which was subsequently added triethylamine (4.5 ml). With cooling in an ice bath, to this was added dropwise 2-chlorobenzoxazole (3.7 ml) in small portions, followed by 45 minutes of stirring. The reaction solution was mixed with water, extracted with methylene chloride and then washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order. The organic layer was dried with magnesium sulfate and the solvent was evaporated under a reduced pressure. Thereafter, the thus obtained mixture was purified by a silica gel column chromatography (methanol) to obtain the title compound 2-(1-piperazinyl)benzoxazole (4.751 g) in the form of yellow crystalline powder.
With potassium carbonate;potassium iodide; In methanol; chloroform; acetonitrile; Reference example 16 Synthesis of 1-(2-benzoxazolyl)piperazine STR79 In 200 ml of acetonitrile were dissolved 33.6 g (0.39 mole) of piperazine and 10.0 g (0.065 mole) of 2-chlorobenzoxazole, and 9.0 g (0.065 mole) of potassium carbonate and a catalytic amount of potassium iodide were added thereto. The mixture was refluxed by heating for 11 hours under stirring. The mixture was cooled to room temperature and then filtered. The filtrate was concentrated under reduced pressure, and the residue was applied to silica gel column chromatography (the eluent used was a mixture of chloroform: methanol = 9: 1) to obtain 7.54 g of 1-(2-benzoxazolyl)piperazine as white crystals. MS spectrum (CI): m/e 204 (M+ +1)
In dichloromethane; water; EXAMPLE 10 8-(Benzoxazol-2-yl)-8-aza-5-azoniaspiro[4,5]decane iodide A 3.07 g portion of 2-chlorobenzoxazole was dissolved in 10 ml of dichloromethane. Under cooling with ice, to this was added dropwise 3.45 g of anhydrous piperazine which has been dissolved in 30 ml of dichloromethane, followed by 1 hour of reaction. The reaction solution was concentrated under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (dichloromethane:methanol=20:1), followed by concentration of the elude under a reduced pressure. Thereafter, the resulting residue was dissolved in 30 ml of water, neutralized with 1N hydrochloric acid, extracted with dichloromethane, washed with water, dehydrated with Na2 SO4 and then concentrated under a reduced pressure to obtain 1.77 g of 2-(1-piperazinyl)benzoxazole.
In ethanol; Preparation 4 1-(Benzoxazol-2-yl)piperazine STR22 To a stirred solution of piperazine (8 g, 93 mmole) in ethanol (30 ml) was added 2-chlorobenzoxazole (3 g, 19.5 mmole) dropwise. The resulting reaction was exothermic. The mixture was then stirred for 18 hours at room temperature, quenched by the addition of methylene chloride (50 ml) and the resulting precipitate removed by filtration. The filtrate was concentrated under reduced pressure then purified by flash column chromatography on silica gel eluding with methylene chloride: methanol: 0.88 ammonia solution (90:10:1) to yield the title compound, m.p. 70-72 (1.8 g, 46%), which was used directly.
With potassium carbonate;potassium iodide; In methanol; chloroform; acetonitrile; (Reference example 16) Synthesis of 1-(2-benzoxazolyl)piperazine 33.6 g (0.39 mol) of piperazine and 10.0 g (0.065 mol) of 2-chlorobenzoxazole were dissolved in 200 ml of acetonitrile, and 9.0 g (0.065 mol) of potassium carbonate and a catalytic amount of potassium iodide were added thereto, followed by heating under reflux with stirring for 11 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography (eluding solution: mixture of chloroform:methanol = 9:1) to obtain 7.54 g of 1-(2-benzoxazolyl)piperazine as white crystals. MS spectrum (CI): m/e 204 (M++1)
With triethylamine; In toluene; at 40℃; for 5h; To a solution of piperazine (2.24 g, 26 mmol, 1 equiv.) in toluene was added 2-chlorobenzoxazole (1.0 g, 6.51 mmol, 1 equiv.), followed by Et3N (3.62 mL, 4 equiv.). The resulting mixture was stirred at 40 C. for 5 hours. The solvent was removed under reduced pressure, and the residue was dissolved in EtOAc. The solution was washed with H2O (*4), brine and dried over Na2SO4. The solvent was evaporated under reduced pressure to afford 0.87 g of intermediate IV-A-17.
In chloroform; at 20℃; for 16h; Step i) To a stirred solution of piperazine (560.9 mg, 6.50 mmol) in CHCl3 (16 ml_) was added 2-chlorobenzoxazole (500 mg, 3.25 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hr. CHCl3 was removed and the resulting white solid was dissolved in water. After stirring in water for 30 min, the aqueous layer was extracted with CH2CI2. The combined organic layer was dried over MgSO4, filtered, and concentrated. The white solid (20, 439 mg, 67 %) was used for the next step without purification.

  • 2
  • [ 137-43-9 ]
  • [ 111628-39-8 ]
  • 2-(4-cyclopentyl-1-piperazinyl)benzoxazole [ No CAS ]
  • 3
  • [ 543-59-9 ]
  • [ 111628-39-8 ]
  • 2-(4-n-pentyl-1-piperazinyl)benzoxazole [ No CAS ]
  • 4
  • [ 111628-39-8 ]
  • [ 501083-62-1 ]
  • 6-(4-benzooxazol-2-yl-piperazin-1-yl)-1-(2-hydroxy-phenyl)-hexan-1-one [ No CAS ]
  • 5
  • [ 111628-39-8 ]
  • [ 173061-57-9 ]
  • [ 1026651-20-6 ]
  • 6
  • [ 111628-39-8 ]
  • [ 824958-33-0 ]
  • 6-(4-benzooxazol-2-yl-piperazin-1-yl)-hexanoic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide [ No CAS ]
  • 7
  • [ 111628-39-8 ]
  • 6-amino-7-(4-benzooxazol-2-yl-piperazin-1-yl)-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid [ No CAS ]
  • 8
  • [ 111628-39-8 ]
  • [ 1027904-29-5 ]
  • 9
  • [ 295790-40-8 ]
  • [ 111628-39-8 ]
  • [ 295790-28-2 ]
YieldReaction ConditionsOperation in experiment
72% With trifluoroacetic acid; In dichloromethane; at 22℃; for 4h; General procedure: GP4-2: N-Boc protected amine in DCM (5 volume) was added by TFA (2.5 volume). The mixture was stirred at rt for four hours and monitored by TLC. After consumption of starting material, volatile solvent was removed under reduced pressure and the residue was neutralized by saturated Na2CO3 solution to obtain the slurry, which was extracted by 10% methanol in DCM (3 times). The organic layers were collected, dried and concentrated to give the desired free amine, for direct use for next step.; 2-(piperazin-1-yl)benzothiazole The title compound was prepared according to GP4-2 as light yellow solid. (7.6 g, 97% yield) LC-MS (ESI): [M+1]+=219.9, tR=3.07 min. 1NMR (400 MHz, d6-DMSO) δ 7.75 (d, J=7.7 Hz, 1H), 7.45 (d, J=7.9 Hz, 1H), 7.29-7.25 (m, 1H), 7.08-7.04 (m, 1H), 2.83 (s, 4H). 13C NMR (101 MHz, DMSO) δ 168.39, 152.48, 130.14, 125.88, 121.05, 121.02, 118.45, 49.43, 44.89.
Example 1.3 Starting from 0.2 g (IV-1) (cf. 1.2) and 0.287 g 2-piperazin-1-yl-benzoxazole 0.31 g Example 1.3 are prepared analogously to Example 1.1 (cf. 1.3). The reaction mixture is mixed with water and the product is suction filtered. Analytical HPLC-MS (method A): RT=1.23 min.
  • 11
  • [ 111628-39-8 ]
  • [ 182438-98-8 ]
  • [ 348133-26-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; b. 9-[4-(4-(benzoxazol-2-yl)-piperazin-1-yl)-butyl]-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoro-ethyl)-amide A solution of 0.3 g (0.7 mmol) of <strong>[182438-98-8]9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoro-ethyl)-amide</strong>, 0.2 g (0.98 mmol) of 2-(piperazin-1-yl)-benzoxazole and 1 ml of triethylamine in 10 ml of tetrahydrofuran is refluxed for 48 hours. The reaction mixture is then poured onto water, extracted twice with dichloromethane and the combined organic phases are dried over sodium sulphate. The product is purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=1:1). Yield: 0.15 g (27.2% of theory), Melting point: 128 C.
  • 12
  • [ 628-21-7 ]
  • [ 111628-39-8 ]
  • [ 159731-48-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; A 245 mg portion of potassium carbonate was added to 300 mg of 2-(1-piperazinyl)benzoxazole which had been dissolved in 5 ml of DMF, and the reaction was carried out for 30 minutes. Under cooling with ice, 0.23 ml of 1,4-diiodobutane was added to the resulting solution, and the reaction was carried out for 1 hour at the same temperature and then for 2 hours at room temperature. The reaction solution was concentrated under a reduced pressure, and the resulting residue was dissolved in 300 ml of dichloromethane and extracted three times with 100 ml of water. Thereafter, the aqueous layers were combined and lyophilized. By purifying the residue by Diaion HP-20 (Mitsubishi Chemicals), 175 mg of the title compound was obtained. NMR (CD3 OD) δ: 7.39 (1H, d), 7.36 (1H, d), 7.23 (1H, t), 7.12 (1H, t), 4.06 (4H, brs), 3.75 (4H, t), 3.70 (4H, t), 2.28 (4H, brs)
  • 13
  • [ 15448-58-5 ]
  • [ 111628-39-8 ]
  • 2-[4-(2-Benzoxazolyl)-1-piperazinyl]-3-hydroxy-1,4-naphthalenedione [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; dichloromethane; EXAMPLE 64 2-[4-(2-Benzoxazolyl)-1-piperazinyl]-3-hydroxy-1,4-naphthalenedione A mixture of 3.48 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone, 2.03 g of 2-(1-piperazinyl)benzoxazole and 200 ml of absolute ethanol was stirred for 18 hours and then filtered. The filtrate was concentrated to dryness and the residue flash chromatographed, eluding with dichloromethane, then 1% methanol in dichloromethane. The desired fraction was evaporated, then recrystallized twice from dichloromethane/ethanol, giving 533 mg of the desired product, mp 190 C. (dec.).
  • 14
  • [ 111628-39-8 ]
  • 1-methylamino-6,7-difluoro-8-difluoromethoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid [ No CAS ]
  • 6-fluoro-8-difluoromethoxy-1,4-dihydro-4-oxo-1-methylamino-7-[4-(2-benzoxazolyl)piperazin-1-yl]quinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
(Preparation example 156) Synthesis of 1-methylamino-6-fluoro-8-difluoromethoxy-1,4-dihydro-4-oxo-7-[4-(2-benzoxazolyl)piperazin-1-yl]quinoline-3-carboxylic acid Reaction of 1-methylamino-6,7-difluoro-8-difluoromethoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid with 1-(2-benzoxazolyl)piperazine and purification of the reaction mixture were carried out in a similar manner to that described in Preparation example 1 to afford the title compound.
  • 15
  • [ 35231-44-8 ]
  • [ 111628-39-8 ]
  • [ 1072879-88-9 ]
  • 16
  • BF2*C11H8ClNO3 [ No CAS ]
  • [ 111628-39-8 ]
  • [ 1056878-97-7 ]
  • 17
  • [ 1056879-05-0 ]
  • [ 111628-39-8 ]
  • [ 1056879-08-3 ]
  • 18
  • [ 75001-52-4 ]
  • [ 111628-39-8 ]
  • [ 1056879-18-5 ]
  • 19
  • C23H32O7S [ No CAS ]
  • [ 111628-39-8 ]
  • C33H41N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20 - 70℃; To a stirred solution of mesylate 109 (200 mg, 0.44 mmol) in DMF (4.4 mL) was added 2-piperazin-1 -ylbenzoxazole (128,4 mg, 0.63 mmol) and triethylamine (0.198 mL, 1.42 mmol) at room temperature. The reaction mixture was heated to 70 C overnight and then cooled down to room temperature, The reaction mixture was poured into NaHCO3 (aq) solution and extracted with dichloromethane (50 mL x 2). The combined organic layer was washed with H2O and brine solution, dried over MgSO4, filtered and concentrated by. The crude product was purified by flash chromatography (10 % MeOH/ CH2CI2) to give 122 mg of the titie compound. MH+ 561
  • 20
  • [ 869488-91-5 ]
  • [ 111628-39-8 ]
  • C25H33F2N5O4 [ No CAS ]
  • 21
  • [ 1203701-93-2 ]
  • [ 111628-39-8 ]
  • [ 1203799-94-3 ]
  • 22
  • [ 111628-39-8 ]
  • [ 234107-57-4 ]
  • C27H25N5O6 [ No CAS ]
  • 23
  • 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole [ No CAS ]
  • [ 111628-39-8 ]
  • [ 1092847-72-7 ]
YieldReaction ConditionsOperation in experiment
50% With lithium perchlorate; In acetonitrile; for 24h;Heating / reflux; Step 20.60 g (2.4 mmol) of an oxirane compound was dissolved in acetonitrile in a dried round flask provided with nitrogen gas, 0.50 g (2.4 mmol) of the compound obtained in Step 1 and 0.39 g (3.7 mmol) of lithium perchlorate were added thereto, and the mixture was refluxed with stirring for 24 hrs. After adding distilled water and ethyl acetate thereto, the aqueous layer was further extracted with an organic solvent(more than 3 times), and the formed organic layer was washed with a saturated NaCl solution, dried over anhydrous magnesium sulfate and filtered. The resulting solution was distilled under a reduced pressure, and the residue was subjected to silica gel column chromatography (dichloromethane:methanol=49:l) to obtain 0.54 g of the title compound (yield: 50%).
  • 24
  • [ 111628-39-8 ]
  • [ 540475-57-8 ]
  • [ 1258527-71-7 ]
YieldReaction ConditionsOperation in experiment
41% With triethylamine; In N,N-dimethyl-formamide; at 20 - 80℃; for 16h; Step 2) To as stirred solution of 7 (200 mg, 0.358 mmol) in DMF (3.60 ml_) was added piperazine 20 (182 mg, 0.511 mmol) and Et3N (160. 7 μL, 1.15 mmol) at room temperature. The reaction mixture was heated to 70-80 C for 16 hr. After cooling down to room temperature, the reaction mixture was poured into sat. NaHCO3 (aq) solution and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and concentrated. The resulting crude product was purified by flash column chromatography on silica gel eluting with 10 % MeOH in CH2CI2 to afford the desired product, 6-1 (98 mg, 41 %).
  • 25
  • [ 56675-37-7 ]
  • [ 111628-39-8 ]
  • (S)-2-amino-1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-3-(thiophen-2-yl)propan-1-one hydrochloride [ No CAS ]
  • 26
  • [ 56675-37-7 ]
  • [ 111628-39-8 ]
  • [ 1312762-81-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 18h;Cooling with ice; STEP A: 2-Piperidino-1,3-benzoxazole (203.6 mgs, 1.00 mmol), N-hydroxybenzotriazole hydrate (138.2 mg, 1.02 mmol) and Boc-β-(2-thienyl)-L-alanine (272.6 mgs, 1.00 mmol) in dichloromethane (10 mL) was cooled in an ice bath, then treated with triethylamine (0.30 mL, 2.15 mmol) and 1-[3-dimethylaminopropyl]-3-ethyl carbodiimide hydrochloride (199.5 mg, 1.04 mmol). The resulting mixture was stirred overnight at room temperature. After 18 h, the resulting mixture was diluted with chloroform and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated to a residue. The residue was purified by flash column chromatography, eluting with 3% methanol in chloroform to yield (S)-tert-butyl 1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate as a colorless glass. 1HNMR (DMSO-d6) δ 8.31 (s, 1H), 7.36 (d, J=7.83 Hz, 1H), 7.33-7.29 (m, 2H), 7.19-7.14 (m, 1H), 7.06-7.01 (m, 1H), 6.94-6.92 (m, 2H), 4.66-4.53 (m, 1H), 3.80-3.54 (m, 8H), 3.25-0.00 (m, 2H), 1.36 (s, 9H); MS (MH+)=457.
  • 27
  • [ 405279-59-6 ]
  • [ 111628-39-8 ]
  • [ 1222786-24-4 ]
  • 28
  • [ 59762-06-0 ]
  • [ 111628-39-8 ]
  • [ 1318753-88-6 ]
  • 29
  • [ 401564-36-1 ]
  • [ 111628-39-8 ]
  • [ 401566-37-8 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of 7a (450 mg, 1.50 mmol), 1-(4-chloroisoquinolin-1-yl)piperazine (446 mg, 1.80 mmol) and acetic acid (0.090 mL, 1.6 mmol) in 1,2-dichloroethane (8 mL) was added sodium triacetoxyborohydride (636 mg, 3.00 mmol) and the mixture was stirred at room temperature for 3 h. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressure. The residue purified by silica gel chromatography with chloroform/methanol (50:1, v/v) to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(4-chloroisoquinolin-1-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine (596 mg, 75%) as a white powder.The above compound (592 mg, 1.11 mmol) was dissolved in 1.1 mol/L hydrogen chloride in methanol (10 mL), and the mixture was stirred at room temperature for 5 days. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized with ethanol to give the title compound (318 mg, 52%) as a pale-yellow powder.
  • 30
  • [ 157160-99-1 ]
  • [ 111628-39-8 ]
  • C22H24N4O5 [ No CAS ]
  • 31
  • [ 15084-51-2 ]
  • [ 111628-39-8 ]
  • [ 695221-93-3 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine; In dichloromethane; at 0 - 20℃; for 6h; General procedure: 2-(Piperazin-1-yl)benzazolyl derivatives 8a-d (1 equivalent) and triethylamine (1.5 equivalents) were dissolved in 25 ml dry CH2Cl2 and cooled to 0C in an ice salt bath. Then the required phenylsulfonyl chloride (1.1 equivalents) dissolved in 20 ml dry CH2Cl2 was added dropwise. After the addition, the reaction mixture was stirred at 0C for a further 1h and then allowed to warm to room temperature and the course of the reaction followed by TLC. After completion, the mixture was diluted with additional 50 ml of CH2Cl2 and extracted with 10% NaHCO3 solution (3 x 50 ml). The organic phase was washed with dist. H2O, sat. NaCl solution, dried over anhyd. Na2SO4, filtered and evaporated to dryness. The product was recrystallised from the appropriate solvent, the precipitate formed was filtered under suction and dried at 60C under high vacuum.
  • 32
  • [ 111628-39-8 ]
  • [ 1423160-42-2 ]
  • 33
  • [ 111628-39-8 ]
  • [ 1423160-43-3 ]
  • 34
  • [ 111628-39-8 ]
  • [ 1423160-44-4 ]
  • 35
  • [ 111628-39-8 ]
  • [ 1423160-45-5 ]
  • 36
  • [ 111628-39-8 ]
  • [ 1423160-46-6 ]
  • 37
  • [ 111628-39-8 ]
  • [ 1423160-47-7 ]
  • 38
  • [ 111628-39-8 ]
  • [ 1423160-48-8 ]
  • 39
  • [ 111628-39-8 ]
  • [ 1423160-49-9 ]
  • 40
  • [ 111628-39-8 ]
  • [ 1423160-50-2 ]
  • 41
  • [ 111628-39-8 ]
  • 2-(5-(3-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)propylthio)-1,3,4-oxadiazol-2-yl)-N-phenylacetamide [ No CAS ]
  • 42
  • [ 109-64-8 ]
  • [ 111628-39-8 ]
  • [ 1423160-39-7 ]
  • 43
  • [ 1616493-36-7 ]
  • [ 111628-39-8 ]
  • [ 1616492-97-7 ]
  • 44
  • [ 111628-39-8 ]
  • [ 1621684-23-8 ]
  • 45
  • [ 111628-39-8 ]
  • [ 1621684-14-7 ]
  • 46
  • [ 111628-39-8 ]
  • [ 1621684-25-0 ]
  • 47
  • [ 111628-39-8 ]
  • [ 1621684-15-8 ]
  • 48
  • [ 111628-39-8 ]
  • [ 627-18-9 ]
  • [ 1668599-81-2 ]
YieldReaction ConditionsOperation in experiment
77% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 90℃; for 5h; A solution of 2-piperazin-1 -yl-1 ,3-benzoxazole (0.48 g, 2,4 mmol), 3- bromo-1 -propanol (0.36 g, 2.6 mmol, 1 .1 eq.) and DIPEA (0.41 mL, 2.4 mmol, 1 eq.) in MeCN (10 mL) was stirred at 90 ^ for 5 hours. After the mixture was allowed to cool down, water (10 mL) was added. The mixture was extracted with DCM (3X20 mL). The organic phases were combined and washed with water (2X5 mL), dried over MgS04 and concentrated under reduced pressure. The product was purified by flash silica chromatography (DCM : Methanol = 90 : 10) to afford [4-(1 ,3-benzoxazol-2-yl)piperazin-1 -yl]propan-1 -ol (0.47 g, 77 %). ESI-MS m/z: 262 ([M+H]+, 100%); RT= 0.95 min(Method 3).
  • 49
  • [ 57-57-8 ]
  • [ 111628-39-8 ]
  • [ 1621684-24-9 ]
YieldReaction ConditionsOperation in experiment
75% In toluene; at 105℃; for 0.333333h; A solution of 2-piperazin-1 -yl-1 ,3-benzothiazole (0.5 g, 2.3 mmol) and oxetan-2-one (0.43 mL, 6.9 mmol, 3 eq.) in toluene (20 mL) was stirred at 105<C for 20 minutes. After the mixture was allowed to cool down, the mixture was concentrated under reduced pressure. Water (20 mL) was added and the mixture was extracted with ethyl acetate (3X200 mL). The combined organic phases were dried over MgS04and concentrated under reduced pressure affording 1 -[4-(1 ,3-benzothiazol-2-yl)piperazin-1 -yl]-3-hydroxy- propan-1 -one (0.5 g, 75%). ESI-MS m/z: 292 ([M+H]+), 100%); RT= 1 .38 min(Method 3).
  • 50
  • [ 95-55-6 ]
  • [ 111628-39-8 ]
  • 51
  • [ 110-85-0 ]
  • [ 2382-96-9 ]
  • [ 111628-39-8 ]
YieldReaction ConditionsOperation in experiment
71% In toluene; at 150℃; for 16h; In a 100ml round bottom flask was placed 0.604g (4mmol) of benzoxazole and 0.688g (8 mmol) of anhydrouspiperazine or substituted piperazine derivative. 50 ml of drytoluene was added to this mixture and the contents werestirred and refluxed over an oil bath maintained at 150C for16-18 hours. After this period, the mixture was cooled andthe solvent was rotary evaporated and the residue wassubjected to column chromatography over silica gel usingmethanol/methylene chloride (20/80) to furnish the titledcompounds.
  • 52
  • C12H11FN2O [ No CAS ]
  • [ 111628-39-8 ]
  • (R)-2-(4-((1-(1-(4-fluorophenyl)ethyl)-1H-imidazol-5-yl)methyl)piperazin-1-yl)benzo[d]oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
50 mg A mixture compound of compound Int 1-4 (100 mg, 0.49 mmol), and 2-(piperazin-l- yl)benzo[d]oxazole (107 mg, 0.49 mmol) in 1 ,2-dichloromethane was stirred at room temperature for 3h. NaBH(OAc)3 (311 mg, 1047 mmol) was added and the mixture was stirred for 16 hours, diluted with H20 and extracted with CH2CI2 (3x5 mL). The combined organic extracts were washed with H20 (3x5 mL) and brine, dried (Na2S04) and concentrated . The residue was purified by HPLC to afford 50 mg of Compound 23. H NMR (CD3OD) δ 9 9.23 (s, 1H), 7.60 (s, 1H), 7.35-7.29 (m, 4H), 7.24-7.21 (m, 1H), 7.20-7.10 (m, 3H), 6.06 (d, J=6.8 Hz, 1H), 3.67-3.59 (m, 5H), 3.48 (d, J=14.8 Hz, 1H), 2.64-2.55 (m, 4H), 1.94 (d, J=6.8 Hz, 3H). MS (ESI) m/z(M+l): 406.
50 mg A mixture compound of compound Tnt 1-4 (100 mg, 0.49 mmol), and <strong>[111628-39-8]2-(piperazin-1-yl)benzo[d]oxazole</strong> (107 mg, 0.49 mmol) in 1,2-dichioromethane was stirred at roomtemperature for 3h. NaBH(OAc)3 (311 mg, 1047 mmol) was added and the mixture was stirred for 16 hours, diluted with H20 and extracted with CH2C12 (3x5 mL). The combined organic extracts were washed with H20 (3 x5 mL) and brine, dried (Na2SO4) and concentrated. The residue was purified by HPLC to afford 50 mg of Compound 23. ‘H NMR (CD3OD) ö 9 9.23(s, 1H), 7.60 (s, 1H), 7.357.29 (m, 4H), 7.247.21 (m, 1H), 7.207.10 (m, 3H), 6.06 (d,J=6.8 Hz, 1H), 3.673.59 (m, 5H), 3.48 (d, J=14.8 Hz, 1H), 2.642.55 (m, 4H), 1.94 (d, J6.8 Hz, 3H). MS (ESI) mlz(M+1): 406.
  • 53
  • 2',3'-o-isopropylideneadenosine-5-carboxylic acid [ No CAS ]
  • [ 111628-39-8 ]
  • C24H26N8O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In acetonitrile; at 20℃; for 3h;Automated synthesizer; General procedure: Approximately 0.5 mmol of 2 and 0.5 mmol of HATU were dispensed in 24 reaction wells (MiniBlock XT) using a dispensing spatula and funnel. To each well were added 10 mL of anhydrous MeCN, (0.5 mmol) of the appropriate amine in MeCN, and then 0.13 mL of DIPEA (0.75 mmol) through the septa sheet. The reaction block was covered and shaken at room temperature for 180 minutes (TLC monitored). Two grams of silica gel were added to each well and the reaction block was placed on a parallel centrifugal evaporator. After automated flash chromatography, the obtained pure intermediate (0.25 mmol) and 4 mL of formic acid (50%) were dispensed in 24 reaction wells (MiniBlock XT), heated to 70 C and shaken vigorously for 2 h whereupon TLC showed no remaining starting material. Silica gel (1 g) was added to each well and the mixture was evaporated, dried on a parallel centrifugal evaporator and the dry solid was chromatographed to give the desired product.
  • 54
  • 2-(isocyanomethyl)thiophene [ No CAS ]
  • [ 123-38-6 ]
  • [ 111628-39-8 ]
  • 2-(4-(1-(1-(thiophen-2-ylmethyl)-1H-tetrazol-5-yl)propyl)piperazin-1-yl)benzoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% General procedure: GP4-1: A mixture of substituted2-chlorobenzothiazole (1.0eq), N-Bocpiperazine (1.05 eq) and Na2CO3 (1.2 eq) inDMF (10 volume) was heated up at 100 0C for hours, the process ofwhich was monitored by TLC. The mixture was diluted by EA and added by water.After extraction by EA (2 times), the collected organic layers were washed by10% citric acid, and then brine, dried over Na2SO4 andconcentrated to give crude product, which could be used directly withoutfurther purification.GP4-2: N-Bocprotected amine in DCM (5 volume) was added by TFA (2.5 volume). The mixturewas stirred at rt for four hours and monitored by TLC. After consumption ofstarting material, volatile solvent was removed under reduced pressure and theresidue was neutralized by saturated Na2CO3 solution toobtain the slurry, which was extracted by 10% methanol in DCM (3 times). Theorganic layers were collected, dried and concentrated to give the desired freeamine, for direct use for next step.GP4-3: Free amine (1.0 eq) suspendedin DCM (10 volume) was added by aldehyde (1.1 eq) under N2atmosphere. The mixture was stirred at rt 15 min. Then trimethylsilylazide(TMSN3, 1.1 eq) was added, and stirring was kept foranother 15 min, followed by addition of isonitrile (1.0 eq). The mixture wasstirred at for 12 h. After removal of solvent, the residue was purified bypreparative TLC (DCM/MeOH as eluent) to give the product, which could bere-purified by trituration with ether.
  • 55
  • [ 195390-64-8 ]
  • [ 111628-39-8 ]
YieldReaction ConditionsOperation in experiment
89% With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 3h; tert-Butyl 4-(benzo[d]oxazol-2-yl)piperazine-1-carboxylate (103, 500mg, 1.65mmol) was dissolved in CH2Cl2 (15mL), cooled to 0C and TFA (2mL) was added. The mixture was stirred for 3hat rt and the solvent was removed under reduced pressure. The crude product was dissolved in MeOH, K2CO3 (3.6g, 25.96mmol) was added and the mixture was stirred for 5minat 5C. The mixture was filtered and the solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted 3-times with EtOAc (50mL). The organic extracts were combined, dried over MgSO4 and the solvent was evaporated under reduced pressure to afford 298mg (1.47mmol, 89%) of 104. TLC: RF=0.17 (SiO2, CH2Cl2/MeOH, 10:1); 1H NMR (250MHz, CDCl3, 300K): δ=7.36 (d, 3J=7.5Hz, 1H), 7.26 (d, 3J=7.9Hz, 1H), 7.17 (dt, 3J=7.7, 1.1Hz, 1H), 7.04 (dt, 3J=7.7, 1.1Hz, 1H), 3.89-3.65 (m, 4H), 3.17-2.96 (m, 4H) ppm; MS (ESI pos.): m/z (%)=204.27 (100) ([M+H]+, calcd. 204.11).
72% With trifluoroacetic acid; In dichloromethane; at 20℃; for 4h; General procedure: GP4-1: A mixture of substituted2-chlorobenzothiazole (1.0eq), N-Bocpiperazine (1.05 eq) and Na2CO3 (1.2 eq) inDMF (10 volume) was heated up at 100 0C for hours, the process ofwhich was monitored by TLC. The mixture was diluted by EA and added by water.After extraction by EA (2 times), the collected organic layers were washed by10% citric acid, and then brine, dried over Na2SO4 andconcentrated to give crude product, which could be used directly withoutfurther purification.GP4-2: N-Bocprotected amine in DCM (5 volume) was added by TFA (2.5 volume). The mixturewas stirred at rt for four hours and monitored by TLC. After consumption ofstarting material, volatile solvent was removed under reduced pressure and theresidue was neutralized by saturated Na2CO3 solution toobtain the slurry, which was extracted by 10% methanol in DCM (3 times). Theorganic layers were collected, dried and concentrated to give the desired freeamine, for direct use for next step.GP4-3: Free amine (1.0 eq) suspendedin DCM (10 volume) was added by aldehyde (1.1 eq) under N2atmosphere. The mixture was stirred at rt 15 min. Then trimethylsilylazide(TMSN3, 1.1 eq) was added, and stirring was kept foranother 15 min, followed by addition of isonitrile (1.0 eq). The mixture wasstirred at for 12 h. After removal of solvent, the residue was purified bypreparative TLC (DCM/MeOH as eluent) to give the product, which could bere-purified by trituration with ether.
  • 57
  • [ 111628-39-8 ]
  • 3-(4-benzoxazol-2-yl-piperazin-1-sulfonyl)-N-hydroxybenzamide [ No CAS ]
  • 58
  • [ 111628-39-8 ]
  • 4-(4-benzoxazol-2-yl-piperazin-1-sulfonyl)-N-hydroxybenzamide [ No CAS ]
  • 59
  • [ 111628-39-8 ]
  • C21H21N3O7S [ No CAS ]
  • 60
  • [ 111628-39-8 ]
  • C21H21N3O7S [ No CAS ]
  • 61
  • [ 4025-64-3 ]
  • [ 111628-39-8 ]
  • 3-(4-benzoxazol-2-yl-piperazin-1-sulfonyl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine; In tetrahydrofuran; dichloromethane; at 0 - 20℃; General procedure: 2-(Piperazin-1-yl)benzazolylderivatives 5a-d (1 equivalent) and triethylamine (1.5 equivalents) were dissolved in25 mL dry CH2Cl2 and cooled to 0C in an ice salt bath. Then the required 3 or 4-Chloro-sulfonylbenzoicacid (1.1 equivalents) dissolved in 15 mL dry THF was added dropwise. After theaddition, the reaction mixture was stirred at 0C for a further 1 h and then allowed to warm toroom temperature and the course of the reaction followed by TLC (CH2Cl2/MeOH/konz. NH3:898/100/2). After indicating the end of the reaction, the mixture was evaporated to dryness, the residue was dissolved in dist. water and made slightly acidic (pH 6) with glacial acetic acid andstirred for about 30 mins. The solid formed was filtered by suction, washed with water andthen with petrol ether. The product was recrystallized from the appropriate solvent; the precipitateformed was filtered under suction and dried at 60C under high vacuum.
  • 62
  • [ 10130-89-9 ]
  • [ 111628-39-8 ]
  • 4-(4-benzoxazol-2-yl-piperazin-1-sulfonyl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine; In tetrahydrofuran; dichloromethane; at 0 - 20℃; General procedure: 2-(Piperazin-1-yl)benzazolylderivatives 5a-d (1 equivalent) and triethylamine (1.5 equivalents) were dissolved in25 mL dry CH2Cl2 and cooled to 0C in an ice salt bath. Then the required 3 or 4-Chloro-sulfonylbenzoicacid (1.1 equivalents) dissolved in 15 mL dry THF was added dropwise. After theaddition, the reaction mixture was stirred at 0C for a further 1 h and then allowed to warm toroom temperature and the course of the reaction followed by TLC (CH2Cl2/MeOH/konz. NH3:898/100/2). After indicating the end of the reaction, the mixture was evaporated to dryness, the residue was dissolved in dist. water and made slightly acidic (pH 6) with glacial acetic acid andstirred for about 30 mins. The solid formed was filtered by suction, washed with water andthen with petrol ether. The product was recrystallized from the appropriate solvent; the precipitateformed was filtered under suction and dried at 60C under high vacuum.
  • 63
  • (5R)-2-chloro-5-oxido-N-tetrahydropyran-4-yl-6,7-dihydrothieno[3,2-d]pyrimidin-5-ium-4-amine [ No CAS ]
  • [ 111628-39-8 ]
  • (R)-2-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-4-((tetrahydro-2H-pyran-4-yl)amino)-6,7-dihydrothieno[3,2-d]pyrimidine 5-oxide [ No CAS ]
  • 64
  • [ 110-85-0 ]
  • [ 273-53-0 ]
  • [ 111628-39-8 ]
YieldReaction ConditionsOperation in experiment
With tetra-(n-butyl)ammonium iodide; acetic acid; In acetonitrile; at 20℃;Electrochemical reaction; Green chemistry; General procedure: A 30 mL screw capped vial with a septum was inserted carbon anode and aluminum cathode (CAUTION: Electrodes should not come in contact with each other). The electrodes were connected to a cell phone charger (5V) by use of alligator clips. To the reaction vial were added benzoxazole 1 (119 mg, 1 mmol), N-Boc piperazine 2a (372 mg, 2 mmol), acetic acid (300 mg, 5 mmol, 5 equiv.) and TBAI (37 mg, 10 mol%) and the mixture was dissolved in 20mL of acetonitrile and stirred gently at room temperature. Electric current was passed through the reaction vial at room temperature for 3 h. The progress of the reaction was monitored by TLC and LC-MS. After the completion of the reaction, the solvent was removed in vacuo and the crude material was re-dissolved in ethyl acetate (25 mL) and then washed with saturated aqueous sodium carbonate solution (3×10mL). The organic layer was separated, washed with water and then dried over sodium sulfate. The product was purified by column chromatography using hexane and ethyl acetate as eluent to afford 282 mg of compound 3a (93 % yield).
  • 65
  • [ 111628-39-8 ]
  • (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-cyclohexylbutanoic acid [ No CAS ]
  • (S)-(9H-fluoren-9-yl)methyl (1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-4-cyclohexyl-1-oxobutan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% General procedure: The carboxylic acid (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-cyclohexylbutanoic acid (71, 1 eq) and HATU (1.2 eq) were dissolved in DMF (8mL) and DIPEA (1.2 eq) was added. The solution was stirred at rtrt for 1.5h and the corresponding amine (1.2 eq) was added, either pure when liquid or diluted in DMF (4mL) when solid. The mixture was stirred for 20hat rt. CH2Cl2 or EtOAc (50mL) was added and the organic phase was washed 4 times with water (50mL) and dried over MgSO4. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica (eluent: cyclohexane/EtOAc, CH2Cl2/MeOH or EtOAc/MeOH) if not stated otherwise.
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