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[ CAS No. 896464-16-7 ]

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Chemical Structure| 896464-16-7
Chemical Structure| 896464-16-7
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Product Details of [ 896464-16-7 ]

CAS No. :896464-16-7 MDL No. :MFCD09839640
Formula : C12H22N2O2 Boiling Point : 319.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :226.32 g/mol Pubchem ID :24820512
Synonyms :

Safety of [ 896464-16-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 896464-16-7 ]

  • Downstream synthetic route of [ 896464-16-7 ]

[ 896464-16-7 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 896464-11-2 ]
  • [ 896464-16-7 ]
  • 2-[4-(5-methyl-2H-pyrazol-3-ylamino)-pyrido[2,3-d]pyrimidin-2-yl]-2,7-diaza-spiro[3,5]nonane-7-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 105℃; for 1h; Example 2; 1-(2-r4-(5-Methyl-2H-pyrazol-3-ylamino)-pyridor2,3-cnpyrimidin-2-yl1-2.7-diaza-spiror3.51non-7-yl)-ethanone; (A) Preparation of 2-r4-(5-Methyl-2H-pyrazol-3-ylamino)-pyridor2,3-dlpyrimidin-2-yll-2.7-diaza-spiror3.51nonane-7-carboxylic acid tert-butyl ester; Heat a solution of 2-Chloro-N- (3-methyl-1 H-pyrazol-5-yl) pyrido[2,3-d]pyrimidine-4- amine (1.5g, 5.76 mmol), t-butyl 2,7-duazaspiro [3,5]nonane-7-carboxylate (1.43 g, 6.35 mmol), and N,N-diisopropylethylamine (6.35 mmol, 1.10 mL) in 1-methyl-2-pyrrolidinone (6.0 mL) at105 0C for 1 h. Cool the reaction to room r.t., dilute with CH2CI2 and wash with Brine. Dry the organic layer over Na2SO4. Concentrate and dilute with EtOAc to provide a solid. Utilize compound without further purification.
  • 2
  • [ 624-28-2 ]
  • [ 896464-16-7 ]
  • [ 1032158-27-2 ]
YieldReaction ConditionsOperation in experiment
52% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 175℃; for 0.166667h;Microwave irradiation; A mixture of 2,5-dibromopyridine (474 mg, 0.0002 mol), 2,7-diazaspiro[3.5]nonane- 7-carboxylic acid, 1,1-dimethylethyl ester (CAS: 896464-16-7, 500 mg, 0.00019 mol), DIPEA (2 ml) in acetonitrile (1 ml) was heated at 175 0C under microwave irradiation for 10 minutes. Then DCM and Na2CO3 (aqueous saturated solution) were added. The organic layer was separated, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by flash chromatography (eluent: DCM and DCM/EtOAc 4:1 ) to obtain 375 mg of intermediate compound 1-10 (52 %).
  • 3
  • [ 896464-16-7 ]
  • [ 959960-89-5 ]
  • [ 1032158-36-3 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 2,3,4-trifluorotoluene; at 100℃; for 24h; A mixture of intermediate compound 1-3 (228 mg, 0.0005 mol), 2,7-diazaspiro[3.5]- nonane7-carboxylic acid, 1,1-dimethylethyl ester (CAS: 896464-16-7, 171 mg, 0.00065 mol), Pd(OAc)2 (11 mg, 0.00005 mol), Xantphos (58 mg, 0.0001 mol), and Cs2CO3 (407 mg, 0.00125 mol) in trifluorotoluene (3.0 ml) was stirred under N2 atmosphere and heated at 100 0C for 24 hours. Then DCM was added. The solids were filtered off through celite and the filtrate was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM and DCM/EtOAc; 9/1 and DCM/ Acetone 9/1 and 4/1), yielding 0.130 g of the BOC-protected compound. This compound was solved in TFA (1 ml) and DCM (2 ml) and the reaction mixture was stirred at room temperature for 2 hours. Then, Na2CO3 (saturated aqueous solution) was added. The organic layer was separated, dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM(MeOH) 95/5 and DCM/(CH3OH/NH3); 95/5). The residue was treated with ethyl ether, yielding 0.0366 g of compound 2-2 (35 %).
  • 4
  • [ 896464-16-7 ]
  • [ 959960-94-2 ]
  • [ 1032158-42-1 ]
YieldReaction ConditionsOperation in experiment
With sodium t-butanolate;palladium diacetate; 2,2'-bis(diphenylphosphino)biphenyl; In toluene; at 100℃; for 24h; A mixture of intermediate compound 1-8 (304 mg, 0.00085 mol), 2,7-diazaspiro[3.5]nonane7-carboxylic acid, 1,1-dimethylethyl ester (CAS: 896464-16-7, 289 mg, 0.0011 mol), Pd(OAc)2 (10 mg, 0.000043 mol), BINAP (40 mg, 0.000064 mol) and 1BuONa (245 mg, 0.00255 mol) in toluene (5 ml) was heated at 100 0C for 24 hours. Then DCM was added. The solid was filtered through celite pad. The filtrate was evaporated, dried over MgSO4 and the residue was purified by column chromatography (eluent: DCM and DCM/ Acetone; 9/1), yielding 0.430 g of the BOC- protected amine. This compound was dissolved in TFA (2 ml) and DCM (4 ml) and the mixture was shaken at room temperature for 2 hours. Then, Na2CO3 (saturated aqueous solution) was added. The organic layer was separated, dried over Na2SO4, and the solvent evaporated. The residue was treated with ethyl ether, yielding 0.278 g of compound 3-3 (81 %).
  • 5
  • [ 896464-16-7 ]
  • [ 959960-87-3 ]
  • [ 1032158-30-7 ]
YieldReaction ConditionsOperation in experiment
67% With sodium t-butanolate;palladium diacetate; 2,2'-bis(diphenylphosphino)biphenyl; In toluene;Sealed tube; Heating / reflux; To a mixture of intermediate compound 1-1 (0.000561 mol) in toluene (3 ml) under N2 atmosphere was added 2,7-diazaspiro[3.5]nonane-7-carboxylic acid, 1,1-dimethylethyl ester (CAS: 896464-16-7, 0.00078 mol), Pd(OAc)2 (0.0000267 mol), BINAP (0.000042 mol) and finally 1BuONa (0.00168 mol). The mixture was refluxed in a sealed tube overnight. Then, H2O was added to the mixture and extracted with DCM. The organic layer was filtered, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography over silica gel (1O g cartridge; eluent: DCM and DCM/ <n="41"/>(CH3OH/NH3); 10 % to 30 %) to obtain 0.189 g of a BOC-protected compound (67 %). This compound (0.00717 mol) was dissolved in TFA (14 ml) and DCM (28.8 ml). The reaction mixture was stirred at room temperature for 2 hours. The solvent was concentrated and the residue was neutralized with NaOH 50 % under ice cool bath. The organic phase was extracted with DCM, dried over Na2SO4 and evaporated. The residue was purified by short column chromatography over silica gel (eluent: DCM/CH3OH; 9.5/0.5 and DCM/(CH3OH(NH3); from 9.5/0.5 to 9/1), yielding 1.08 g of compound 1-5 (49 %).
  • 6
  • [ 896464-16-7 ]
  • [ 1032158-20-5 ]
  • [ 1032158-38-5 ]
YieldReaction ConditionsOperation in experiment
With sodium t-butanolate;palladium diacetate; 2,2'-bis(diphenylphosphino)biphenyl; In toluene; at 100℃; A mixture of intermediate compound 1-5 (0.190 g, 0.00051 mol), 2,7-diazaspiro[3.5]nonane-7-carboxylic acid, 1,1-dimethylethyl ester (CAS:896464-16-7, 0.177 g, 0.00066 mol), Pd(OAc)2 (58 mg, 0.000026 mol), BINAP (24 mg,0.000038 mol), and 1BuONa (147 mg, 0.00153 mol) in deoxigenated toluene (4 ml) was heated overnight at 100 0C. Then, DCM was added. The solid was filtered off and the filtrate was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM and DCM/Acetone; 9/1 and 4/1), yielding 0.202 g of a theBOC-protected compound. This compound (0.202 g, 0.00039 mol) was dissolved inTFA (2 ml) and DCM (4 ml) and stirred at room temperature for 2 hours. Then, Na2CO3 <n="44"/>(saturated aqueous solution) was added. The organic layer was separated, dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM(MeOH) 95/5 and DCM/(CH3OH/NH3); 9/1). Afterwards the residue was treated with DIPE, yielding 0.098 g of compound 3-2 (60 %).
  • 7
  • [ 896464-16-7 ]
  • [ 1032158-25-0 ]
  • [ 1032158-40-9 ]
YieldReaction ConditionsOperation in experiment
91% With sodium t-butanolate;palladium diacetate; 2,2'-bis(diphenylphosphino)biphenyl; In toluene; at 100℃; A mixture of intermediate compound 1-9 (0.040 g, 0.00011 mol), 2,7-diazaspiro[3.5]- nonane7-carboxylic acid, 1,1-dimethylethyl ester (CAS: 896464-16-7, 0.037 g, 0.00014 mol), Pd(OAc)2 (12 mg, 0.0000055 mol), BINAP (5 mg, 0.0000083 mol) and 1BuONa (0.00033 mol) in toluene (1 ml) was stirred under N2 atmosphere and heated overnight at 100 0C. Then, DCM was added. The solid was filtered off through celite and the sol- vent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM and DCM/Acetone 9/1), yielding 0.050 g of the BOC-protected amine (91 %). This product was dissolved in a mixture of TFA (0.5 ml) and DCM (1 ml), stirring the reaction mixture at room temperature for 2 hours. Then, Na2CO3 (aqueous saturated solution) was added. The organic layer was separated, dried over Na2SO4 and the solvent evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM(CH3OH) 95/5 and DCM/(CH3OH/NH3); 1/1). The residue was treated with DIPE, yielding 0.017 g of compound 3-1 (43 %).
  • 8
  • [ 896464-16-7 ]
  • [ 1032157-68-8 ]
  • [ 1032158-34-1 ]
YieldReaction ConditionsOperation in experiment
With sodium t-butanolate;palladium diacetate; 2,2'-bis(diphenylphosphino)biphenyl; In toluene; at 100℃; for 48h; A mixture of intermediate compound 1-11 (185 mg, 0.0005 mol), 2,7-diazaspiro[3.5]- nonane-7- carboxylic acid, 1,1-dimethylethyl ester (CAS: 896464-16-7, 171 mg, 0.00065 mol), Pd(OAc)2 (11 mg, 0.00005 mol), BINAP (23 mg, 0.0375 mmol), and1BuONa (144 mg, 0.0015 mol) in toluene (2.5 ml) was stirred under N2 atmosphere and heated at 100 0C for 24 hours. Excess Of Pd(OAc)2 and BINAP were added while heating the reaction for 24 hours more. Then DCM was added. The solids were filtered off through celite and the filtrate was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM and DCM/EtOAc; 9/1 and DCM/ Acetone9/1 and 4/1), yielding 0.175 g of the BOC-protected compound. This compound was dissolved in TFA (1 ml) and DCM (2 ml) and the reaction mixture was stirred at room temperature for 2 hours. Then, Na2CO3 (saturated aqueous solution) was added. The organic layer was separated, dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent:DCM/MeOH 95/5 and DCM/(CH3OH/NH3); 95/5). The residue was treated with ethyl ether, yielding 0.089 g of compound 2-1 (62 %).
  • 9
  • [ 896464-16-7 ]
  • [ 956034-09-6 ]
  • [ 1093066-66-0 ]
YieldReaction ConditionsOperation in experiment
To a solution of 2-chloro-4-morpholin-4-ylfuro[3,2-£f|pyrimidine-6-carbaldehyde (175 mg, 0.654 mmol) in 1,2-dichloroethane (17 mL) was added 2,7-diazaspiro[3.5]nonane-7- carboxylic acid tert-butyl ester (205 mg, 0.906 mmol). The mixture was stirred at RT for 10 min before adding sodium triacetoxyborohydride (210 mg, 0.991 mmol). The resulting solution was stirred at RT for 18 h. The crude reaction mixture was loaded onto an Isolute SCX-2 cartridge, washed with MeOH then, eluted with 2 M NH3 in MeOH. The resultant residue was purified by column chromatography to give 2-(2-chloro-4-mophiholin-4- ylfuro[3,2-J]pyrimidin-6-ylmethyl)-2,7-diazaspiro[3.5]nonane-7-carboxylic acid tert-butyl <n="48"/>^ester as a white solid. Subsequent BOC-deprotection afforded the title compound as a white solid (186 mg, 76 %).1H NMR (400 MHz, CDCl3): delta 1.71 (m, 4 H), 1.90 (bs, 1 H), 2.68-2.79 (m, 4 H), 3.12 (s, 4 H), 3.73 (s, 2 H), 3.79-3.84 (m, 4 H), 3.93-4.03 (m, 4 H) and 6.54 (s, 1 H).
  • 10
  • [ 896464-16-7 ]
  • [ 34598-49-7 ]
  • tert-Butyl 2-(-(1R)-5-bromo-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate [ No CAS ]
  • 11
  • [ 896464-16-7 ]
  • [ 34598-49-7 ]
  • [ 1314319-10-2 ]
  • tert-butyl 2-((1S)-5-bromo-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate [ No CAS ]
  • 12
  • [ 896464-16-7 ]
  • [ 1313733-32-2 ]
  • [ 1313733-54-8 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 20 - 110℃; To a solution of the appropriate chloride (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- [ajnaphthalene) in degassed dry 1 ,4-dioxane, sodium tert-butoxide (1.7 eq), BINAP (0.09 eq), Pd2(dba)3 (0.05 equiv) and the appropriate amine (ex: 1-BOC- 4-(aminomethyl)piperidine) were added at room temperature. The mixture was refluxed for 6h to 8 h (110C). The reaction mixture was filtered through a Celite pad and washed with DCM. The solvent was removed under vacuum to yield the crude mixture. The residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1% formic acid. Gradient: 40% of A to 0% of A). Amine: <strong>[896464-16-7]2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester</strong>HPLC-MS (method 1): Rt=7.22 min, [M+Hfm/z 576.3.1H NMR (300 MHz, CDCI3) delta 8.59 (s, 1 H), 8.45 (d, J = 8.0 Hz, 1 H), 7.52 (t, J = 8.1 Hz, 1 H), 7.26 (d, J = 2.4 Hz, 1 H), 4.32 - 4.22 (m, 2H), 3.93 (s, 4H), 3.72 (s, 3H), 3.47 (d, J = 6.7 Hz, 2H), 3.44 - 3.35 (m, 4H), 2.04 - 1.94 (s, 9H), 1.84 - 1.73 (m, 4H).
  • 13
  • [ 896464-16-7 ]
  • [ 1332455-32-9 ]
  • [ 1332454-52-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In dimethyl sulfoxide; at 90℃; for 4h; Example2 : tert-butyl 2- [6-(biphenyl-4-ylcarbonyl)-5,6,7,8-tetrahydropyrido [4,3-d] pyrimidin-4-yl] - 2,7-diazaspiro [3.5] nonane-7-carboxylateStep ATo a solution of Intermediate I (300 mg, 0.87 mmol) in anhydrous DMSO (15 mL) was added t-butyl 2, 7- diazaspiro [3.5] nonane-7-carboxylate (685 mg, 2.61 mmol) and K2C03 (360 mg, 2.61 mmol). The mixture was heated to 90C for 4 hrs. The reaction mixture was filtered and he filtrate was evaporated and purified by HPLC to yield compound (350 mg) XH NMR ( MeOD) delta 8.05 ( br, 1H ) , 7.40 ~ 7.69 ( m , J = 8.0 Hz, 2H),7.23(d, J = 7.3Hz, 2H ) , 7.15 ( d , J = 7.8 Hz, 2H ) , 7.02 (t, J =7.6 Hz, H) , 6.95 ( t, J =7.4 Hz, 2H),5.04(s, 1H), 4.02 -4.21 (m, 2H), 3.22 -3.66 (m,9H), 2.50 (s,2H), 1.36- 1.68 (m, 4H), 1.01 ( s, 9H).
  • 14
  • [ 896464-16-7 ]
  • [ 1331742-80-3 ]
  • [ 1331742-84-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In ethanol; at 150℃; Preparation of final product 2-49 The intermediate I-08, 5-chloro-3-(3-trifluoromethoxy-phenyl)-3H-[1,2,3]triazolo[4,5-b]pyridine (0.050 g; 0.159 mmol), 2,7-diaza-spiro[3.5]nonane-7- carboxylic acid tert-butyl ester, hydrochloride, TEA (66 uL; 0.477 mmol) and dry EtOH (2 mL) were mixed and reacted at 150 C sandbath temp overnight. Evaporation and extractive workup (DCM/Bicarb) gave the crude boc-protected compound that was pisolated as a yellow precipitate. It was dissolved in dry methanol (2 mL) and HCI (4M in dioxane, 0.25 mL) was added. Overnight stirring at rt, evaporation and free-basing gave 36 mgs of the final compound 2-49, N- methyl-N'-fS-iS-trifluoromethoxy-pheny -SH-ll ^.Sltriazolo .S-blpyridin-S-yl]- propane-1 ,3-diamine, as a yellow solid (Y: 46%).
  • 15
  • [ 896464-16-7 ]
  • [ 1356471-56-1 ]
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