Acrolein → HCID 135599851, compound

HRID 1175813Notes

Reaction equation

HRID 1175813 reaction equation
[CH3:1][N:2]1CCNCC1.[N:8]12[CH2:18][CH2:17][CH2:16]N=[C:14]1[CH2:13]CC[CH2:10][CH2:9]2.C(C=C)=O.[NH2:23][C:24]1[N:25]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:26]=[C:27]2[C:36]3[CH:35]=[CH:34][C:33]([NH2:37])=[CH:32][C:31]=3[NH:30][C:29](=[O:38])[C:28]=12.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>[Cl-].[Na+].O.O1CCCC1>[NH2:23][C:24]1[N:25]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:26]=[C:27]2[C:36]3[CH:35]=[CH:34][C:33]([NH:37][CH2:16][CH2:17][CH2:18][N:8]4[CH2:9][CH2:10][N:2]([CH3:1])[CH2:13][CH2:14]4)=[CH:32][C:31]=3[NH:30][C:29](=[O:38])[C:28]=12

Participants

9

Reactant 6

HCID 7847AcroleinHCID 531671-MethylpiperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 135599894HCID 135599894, compound

Product 1

HCID 135599851HCID 135599851, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of 1-methylpiperazine (86 μl), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.8 μl) and tetrahydrofuran (6 ml), was cooled to −20° C., acrolein (51.7 μl) was added thereto, and was stirred for 1 hour from −20° C. to −10° C. To the reaction mixture was added 3,7-diamino-2-phenyl-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (100 mg), stirred at 0° C. for 30 minutes, sodium triacetoxyborohydride (268 mg) was added thereto, and stirred at room temperature for 3 hours. The reaction mixture was basified by adding 5% sodium hydrogen carbonate, brine were added thereto and then extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with aminopropylated silica gel column chromatography. To the concentrated residue of fraction was solidified by adding diisopropyl ether-hexane. The solid was collected by filtration, washed with hexane, and dried to obtain the target compound (45 mg).

Workup

  1. stirringstirred at 0° C. for 30 minutes
  2. stirringstirred at room temperature for 3 hours
  3. additionwere added
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified with aminopropylated silica gel column chromatography
  9. additionby adding diisopropyl ether-hexane
  10. filtrationThe solid was collected by filtration
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-00f1129bdbc1478d9d465a724f2f1ce6
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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