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[ CAS No. 788812-21-5 ] {[proInfo.proName]}

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Chemical Structure| 788812-21-5
Chemical Structure| 788812-21-5
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Product Details of [ 788812-21-5 ]

CAS No. :788812-21-5 MDL No. :MFCD22058263
Formula : C12H14N2O Boiling Point : -
Linear Structure Formula :- InChI Key :JKJBINGBZKSOFX-UHFFFAOYSA-N
M.W : 202.25 Pubchem ID :15548169
Synonyms :

Safety of [ 788812-21-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P342+P311-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 788812-21-5 ]

* 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 [ 788812-21-5 ]

[ 788812-21-5 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 209160-93-0 ]
  • [ 788812-21-5 ]
  • 1'-(3-((S)-(3-Chlorophenyl))-4-(N-(phenylsulfonyl)(methylamino))butyl)-spiro(1-oxoisoindoline-3,4'-piperidine) [ No CAS ]
  • 2
  • [ 19926-90-0 ]
  • [ 788812-21-5 ]
  • 1'-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)spiro[isoindoline-1,4'-piperidin]-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 6h; EXAMPLE 3; l'-(bicyclo[2.2.1]hept-S-en-2-ylmethyl)spiro[isoindoline-l,4'-piperidin]-3- one (Compound No. 267); EPO <DP n="75"/> Compound No. 267[00209] Sodium triacetoxyborohydride (31 mg, 0.15 mmol) was added to a stirred solution of spiro[isoindoline-l,4'-piperidin]-3-one 3a (20 mg, 0.10 mmol) and bicyclo[2.2.1]hept-5- ene-2-carbaldehyde (18mg, 0.15mmol) in 1,2-dichloroethane (1 mL) and the mixture was stirred at room temperature for 6 h. The solvent was removed under reduced pressure and the crude product was purified by preparative HPLC (5-70% CH3CN-H2O gradient withθ.05% TFA, 15 min) to give compound no. 267.
  • 3
  • [ 920023-54-7 ]
  • [ 788812-21-5 ]
YieldReaction ConditionsOperation in experiment
To a solution of 0.10 g (0.33 mmol) tert-butyl 3-oxo-2,3-dihydro-1'H-spiro[isoindole-1,4'-piperidine]-1'-carboxylate in 3.3 ml dichloromethane were added 0.25 ml (3.3 mmol) trifluoroacetic acid at room temperature. After stirring for 4 h the reaction mixture was diluted with 20 ml aqueous 1 M sodium hydroxide solution (20 ml) and extracted with ethyl acetate (3*50 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the crude title compound (0.095 g) as a light yellow solid. MS m/e (%): 203 (M+H+, 100).
  • 4
  • [ 788812-21-5 ]
  • 1'-[(6-chloro-1H-indol-3-yl)carbonyl]spiro[isoindole-1,4'-piperidin]-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% To a solution of 0.060 g (0.31 mmol) 6-chloro-1H-indole-3-carboxylic acid in 3 ml dichloromethane were added 0.045 ml (0.38 mmol) 1-chloro-N,N,2-trimethyl-propenylamine at room temperature. After stirring for 1 h the reaction mixture was concentrated in vacuo. The residue was redissolved in 2 ml dry N,N-dimethylformamide. A solution of 0.062 g (0.31 mmol) <strong>[788812-21-5]spiro[isoindole-1,4'-piperidin]-3(2H)-one</strong> and 0.064 ml (0.46 mmol) triethylamine in 1 ml dry N,N-dimethylformamide was added at room temperature. After stirring for 2 h the reaction mixture was quenched with 1 M aqueous sodium hydroxide solution (30 ml) and extracted with ethyl acetate (3*50 ml). The combined organic layers were washed with water (2*30 ml), 0.5 M aqueous hydrochloric acid solution (1*30 ml) and brine (1*30 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was triturated in warm diethyl ether, filtrated and dried in vacuo to give the title compound (0.031 g, 22%) as light brown solid with a purity of approx. 80% by LC-.MS. MS m/e (%): 378 (M-H+, 100).
  • 5
  • [ 920023-68-3 ]
  • [ 788812-21-5 ]
  • 2-{6-chloro-3-[(3-oxo-2,3-dihydro-1'H-spiro[isoindole-1,4'-piperidin]-1'-yl)carbonyl]-1H-indol-1-yl}-N-methylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h; To a solution of 0.35 g (0.13 mmol) 6-chloro-1-methylcarbamoylmethyl-1H-indole-3-carboxylic acid, 0.025 ml (0.14 mmol) N,N-diisopropylethylamine and 0.055 g (0.14 mmol) 0-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate in 2 ml dry N,N-dimethylformamide were added 0.029 g (0.14 mmol) <strong>[788812-21-5]spiro[isoindole-1,4'-piperidin]-3(2H)-one</strong> at room temperature. After stirring for 2 h the reaction mixture was quenched with 0.5 M aqueous sodium hydroxide solution (20 ml) and extracted with ethyl acetate (2*30 ml). The combined organic layers were washed with water (2*30 ml) and brine (1*30 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (aminopropyl-modified silica gel, dichloromethane/methanol) to give the title compound (0.026 g, 44%) as a white solid. MS m/e (%): 451 (M+H+, 100).
  • 6
  • [ 2131-55-7 ]
  • [ 788812-21-5 ]
  • [ 915104-42-6 ]
YieldReaction ConditionsOperation in experiment
70% Preparation 3: N-(4-Chlorophenyl)-3-oxo-2,3-dihydro-1'H-spiro[isoindole-1 ,4'-piperidine]-1'- carbothioamide. The title compound was prepared from <strong>[788812-21-5]spiro[isoindole-1,4'-piperidin]-3(2H)-one</strong> (WO 01/45707, p 83) and 4-chlorophenyl isothiocyanate, using the same method as that described for preparation 1, in 70% yield.1HNMR(400MHz, DMSO-d6) δ: 1.72-1.86(m, 4H), 4.17-4.29(m, 4H), 6.82(d, 1 H), 6.95(m, 1 H), 7.18(m, 1 H), 7.31 (m, 4H), 7.46(d, 1 H), 9.41 (s, 1H),10.45(s, 1 H); LRMS APCI m/z 372 [M+H]+.
  • 7
  • [ 936691-71-3 ]
  • [ 788812-21-5 ]
  • N-methyl-3-oxo-N-(2-piperidin-1-ylethyl)-2,3-dihydro-1'H-spiro[isoindole-1,4'-piperidine]-1'-carboxamide [ No CAS ]
  • 8
  • [ 268538-11-0 ]
  • [ 788812-21-5 ]
  • 3-oxo-N-(5-phenyl-2-pyrazinyl)spiro[isoindoline-1.4'-piperidine]-1'-carboxamide [ No CAS ]
  • 9
  • [ 24424-99-5 ]
  • [ 788812-21-5 ]
  • [ 920023-54-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; acetonitrile; for 3h; Step 2; Crude <strong>[788812-21-5]spiro[isoindoline-1,4'-piperidin]-3-one</strong> was dissolved in 1:1 MeCN:10% aq K2CO3 (20 mL) and Boc2O (50 mg, 0.23 mmol, 2.0 equiv) added. The mixture stirred for 3 h. The solution was evaporated and the mixture was diluted with EtOAc. The organic layer was washed with 1.0 M aq HCl and brine, dried over Na2SO4, and evaporated. The residue was purified by flash chromatography on silica, eluting with 20-80% EtOAc in hexanes to afford tert-butyl 3-oxospiro[isoindoline-1,4'-piperidine]-1'-carboxylate.
  • 10
  • [ 1017540-78-1 ]
  • [ 788812-21-5 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; at 75℃; for 19h; Step 1; Tert-butyl 2-(4-methoxybenzyl)-3-oxospiro[isoindoline-1,4'-piperidine]-1'-carboxylate (50 mg, 0.12 mmol, 1.0 equiv) and TFA (7 mL) were heated to 75 C. for 19 h. After this time LC-MS showed removal of the Boc- and p-methoxybenzyl groups. The mixture was concentrated to leave crude spiro[isoindoline-1,4'-piperidin]-3-one which was used directly.
  • 11
  • 2’,3’-dihydro-1‘H-spiro[isoindole-1,4’-pyridin]-3(2H)-one [ No CAS ]
  • [ 788812-21-5 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at 0 - 20℃; for 3h; NaBH(OAc)3 (856 mg, 4.05 mmol) was added to a 0 C cooled suspension of the compound obtained in step c (326 mg, 1.62 mmol) and AcOH (5 mL) in ACN (5 mL). The reaction mixture was allowed to reach r.t., stirred at this temperature for 3 h and slowly poured into NaHCO3 (saturated aqueous solution, 20 mL). The mixture was taken up to pH 8-9 with NaOH (36% aqueous solution) and extracted with DCM (5x20 mL) and n-BuOH (2x15 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated, to give the title compound as an off-white solid (360 mg,quantitative yield). The crude residue was submitted to next step without purification.HPLC-MS (Method Bi): Ret, 5.61 mm; ESl-MS m/z, 203.1 (M+1).
  • 12
  • [ 788812-21-5 ]
  • 2-(3-oxospiro[isoindoline-1,4'-piperidin]-1'-yl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one [ No CAS ]
  • 13
  • [ 4023-02-3 ]
  • [ 788812-21-5 ]
  • C13H16N4O [ No CAS ]
  • 14
  • [ 79099-07-3 ]
  • [ 788812-21-5 ]
  • 15
  • C18H26N2O3 [ No CAS ]
  • [ 788812-21-5 ]
  • 16
  • [ 609-67-6 ]
  • [ 788812-21-5 ]
  • 17
  • C25H31IN2O4 [ No CAS ]
  • [ 788812-21-5 ]
  • 18
  • [ 937254-73-4 ]
  • [ 788812-21-5 ]
  • 19
  • [ 937254-75-6 ]
  • [ 788812-21-5 ]
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