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Chemical Structure| 184042-60-2 Chemical Structure| 184042-60-2

Structure of 184042-60-2

Chemical Structure| 184042-60-2

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Product Details of [ 184042-60-2 ]

CAS No. :184042-60-2
Formula : C6H14ClFN2
M.W : 168.64
SMILES Code : FCCN1CCNCC1.[H]Cl
MDL No. :MFCD23701442
InChI Key :LFRPLLDKPVAJTL-UHFFFAOYSA-N
Pubchem ID :22281452

Safety of [ 184042-60-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 184042-60-2 ]

* 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 [ 184042-60-2 ]

[ 184042-60-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 184042-60-2 ]
  • 7-oxa-10,13,17,18,21-pentaazatetracyclo[12.5.2.1^{2,6}.0^{17,20}]docosa-1(20),2,4,6(22),14(21),15,18-heptaene hydrochloride [ No CAS ]
  • [ 1429322-96-2 ]
YieldReaction ConditionsOperation in experiment
19% A mixture of 7-oxa-10,13,17,18,21 -pentaazatetracyclo[12.5.2.1A{2,6}.0A{17,20}]docosa- 1 (20),2,4,6(22),14(21 ),-15,18-heptaene hydrochloride (300 mg, 0.904 mmol) and diisopropylethylamine (616 muIota, 3.62 mmol) in tetrahydrofuran (2.5 ml) and N,N-dimethylformamide (2.5 ml) was added drop wise to a solution of di(imidazol- 1 -yl)methanone (220 mg, 1 .356 mmol) in tetrahydrofuran (1 .5 ml). The mixture was stirred at room temperature for 2 hours. 1 -(2-Fluoroethyl)piperazine hydrochloride (229 mg, 1 .36 mmol) was added and the reaction mixture was stirred at 80 C for 63 hours and at 1 10C for 24 hours. Di(imidazol-1 -yl)methanone (150 mg, 0.904 mmol) was added and the mixture was stirred at 1 10 0 C for 18 hours. The solvent was removed under reduced pressure and the residue was purified by reversed phase HPLC (HPLC method A). The product fractions were collected and the solvent was removed under reduced pressure. The product was taken up in dichloromethane/methanol (4:1 , 520 muIota) and 4N HCI in 1 ,4-dioxane (48 muIota, 0.191 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the compound was triturated with diethyl ether, filtered and dried under vacuum.Yield: 84 mg of example 17 (19%)LCMS method 2: MH+ = 454, RT = 2.032 min
  • 2
  • [ 184042-60-2 ]
  • 5'-chloro-7'-oxo-7',8'-dihydro-6'H-spiro[cyclohexane-1,9'-furo[2,3-f]quinazoline]-2'-carboxylic acid [ No CAS ]
  • 5'-chloro-2'-(4-(2-fluoroethyl)piperazine-1-carbonyl)-6'H-spiro[cyclohexane-1,9'-furo[2,3-f]quinazolin]-7'(8'H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 3.5h;Sealed tube; Inert atmosphere; To a mixture of 5'-chloro-7'-oxo-7',8'-dihydro-6'H-spiro[cyclohexane-l,9'-furo[2,3- |quinazoline]-2'-carboxylic acid (Intermediate 15, 50 mg, 0.15 mmol) and l-(2-fluoroethyl) piperazine hydrochloride in DMF (5 mL) was added a solution of N-ethyl-N-isopropylpropan-2- amine (0.08 mL, 0.45 mmol) and 2-(3H-[l,2,3]triazolo[4,5- ?]pyridin-3-yl)- l, 1,3,3- tetramethylisouronium hexafluorophosphate (HATU, 68 mg, 0.18 mmol) in DMF (1 mL). The vial was sealed and the reaction mixture was stirred at room temperature for 3.5 h. The reaction mixture was diluted with water and EtOAc. A precipitate formed in the biphasic mixture, which was filtered, rinsed with H2O and dried under vacuum to give the title compound as a white solid (19 mg, 28%). NMR (400 MHz, DMSO-d6) delta 8.42 (s, 1H), 7.75 (s, 1H), 7.37 (s, 1H), 7.34 (s, 1H), 4.67 - 4.47 (m, 2H), 3.70 (br s, 4H), 2.77 - 2.63 (m, 2H), 2.59 - 2.54 (m, 4H), 2.36 - 2.25 (m, 2H), 1.95 - 1.81 (m, 4H), 1.72 (d, / = 12.7 Hz, 1H), 1.56 (d, / = 14.2 Hz, 2H), 1.35 - 1.22 (m, 1H). [M+H] = 449.0.
 

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