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Acetic Acid → HCID 57786311, compound

HRID 1399211
Notes
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Reaction equation

HRID 1399211 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:23])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]21.C(O[C:27]1(O[Si](C)(C)C)[CH2:29][CH2:28]1)C.[C:35]([BH3-])#N.[Na+].[C:39](O)(=O)[CH3:40]>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:23]([CH:27]2[CH2:28][CH2:29]2)[CH:40]2[CH2:39][CH2:35]2)=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]21
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 577863289-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

Product 1

HCID 57786311HCID 57786311, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine (367 mg, 1.00 mmol), (1-ethoxycyclopropoxy)trimethylsilane (1.01 mL, 5.00 mmol), sodium cyanoborohydride (314 mg, 5.00 mmol), and acetic acid (572 μL, 10.0 mmol) in methanol (3.0 mL) was stirred at reflux for 40 h. The reaction mixture was diluted with ethyl acetate, quenched with aqueous sodium hydrogen carbonate, and filtrated. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20% ethyl acetate/hexane mixture to give the title compound as a colorless solid (83.5 mg, 0.186 mmol, 19%). Analytically pure material was obtained by recrystallization from ethyl acetate/hexane.

Workup

  1. temperatureat reflux for 40 h
  2. customquenched with aqueous sodium hydrogen carbonate
  3. filtrationfiltrated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel eluting with a 20% ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-8346dc4976b6453ea567739f593eb275
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901141B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes