Acetic Acid → HCID 57786039, compound

HRID 1628609Notes

Reaction equation

HRID 1628609 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([N:13]2[C:17]3=[N:18][C:19]4[C:24]([Cl:25])=[CH:23][CH:22]=[C:21]([CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[C:20]=4[N:16]3[CH2:15][CH2:14]2)=[C:9]([CH:12]=1)[CH:10]=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O1CCCC1.O>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([N:13]2[C:17]3=[N:18][C:19]4[C:24]([Cl:25])=[CH:23][CH:22]=[C:21]([CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[C:20]=4[N:16]3[CH2:15][CH2:14]2)=[C:9]([CH2:10][N:2]([CH3:3])[CH3:1])[CH:12]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 57786211HCID 57786211, compound

Product 1

HCID 57786039HCID 57786039, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (2.0 M solution in tetrahydrofuran, 0.096 mL, 0.194 mmol) was added to a solution of 5-chloro-2-[8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl]benzaldehyde (26 mg, 0.0646 mmol) in a mixture of methanol (0.5 mL) and tetrahydrofuran (0.5 mL). After the mixture was stirred for 30 min at room temperature, acetic acid (0.037 mL, 0.0646 mmol) and sodium cyanoborohydride (12 mg, 0.194 mmol) were added. The mixture was stirred at room temperature for 18 hr. The mixture was diluted with water and extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by NH-silica gel column chromatography eluting with a 3-30% ethyl acetate/n-hexane gradient mixture. The desired fractions were concentrated in vacuo, and the resulting solid was triturated with n-hexane to give the title compound (10.3 mg, 0.0239 mmol, 37%) as an amorphous.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hr
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with saturated aqueous sodium hydrogen carbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by NH-silica gel column chromatography
  7. washeluting with a 3-30% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe desired fractions were concentrated in vacuo
  9. customthe resulting solid was triturated with n-hexane

Sources & evidence

ORD record
ord-ff41c9be57704abe9e2b97364785c800
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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