Propanal → HCID 58896420, compound

HRID 2235546Notes

Reaction equation

HRID 2235546 reaction equation
[NH2:1][C:2]1[C:3]([NH:22][CH3:23])=[C:4]([NH:9][C:10]([NH:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])=S)[CH:5]=[C:6]([F:8])[CH:7]=1.C(N([CH2:29][CH3:30])CC)C.[CH:31](=O)[CH2:32][CH3:33].[C:35]([BH3-])#N.[Na+]>C(#N)C.O.CO.C(O)(=O)C>[F:8][C:6]1[CH:7]=[C:2]([N:1]([CH2:35][CH2:29][CH3:30])[CH2:31][CH2:32][CH3:33])[C:3]2[N:22]([CH3:23])[C:10]([NH:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[N:9][C:4]=2[CH:5]=1

Participants

9

Reactant 4

HCID 527PropanalHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 86612999HCID 86612999, compound

Product 1

HCID 58896420HCID 58896420, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 0.29 g (0.87 mmol) of 1-[3-amino-5-fluoro-2-(methylamino)phenyl]-3-mesitylthiourea in 15 mL of acetonitrile was added 1.09 mL (7.9 mmol) of triethylamine followed by 0.4 g (1.5 mmol) of mercuric chloride. After 2h at room temperature an additional 0.7 g (2.6 mmol) of mercuric chloride was added. After 2 h of additional reaction time, the mixture was diluted with water and the resulting crude 5-fluoro-N2-mesityl-1-methyl-1H-benzoimidazole-2,7-diamine was collected as a brown precipitate via filtration. The crude product thus obtained was slurried in 50 mL of methanol and treated with 1.6 mL (22 mmol) of propionaldehyde, 3 mL of glacial acetic acid and 1.1 g (17 mmol) of sodium cyanoborohydride. The mixture was stirred at 50° C. for 24 h. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The crude solid was mixed with water and made basic with saturated potassium carbonate. The mixture was partioned with ethyl acetate and separated. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated onto silica gel and purified by flash chromatography eluting with a 75% hexanes/ethyl acetate mixture to give impure title compound. The impure material was slurried in hexanes and 0.065 g (20%) of the title compound was collected as a white solid.

Workup

  1. filtrationthe resulting crude 5-fluoro-N2-mesityl-1-methyl-1H-benzoimidazole-2,7-diamine was collected as a brown precipitate via filtration
  2. customThe crude product thus obtained
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe volatiles were removed in vacuo
  5. additionThe crude solid was mixed with water
  6. customseparated
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated onto silica gel
  11. custompurified by flash chromatography
  12. washeluting with a 75% hexanes/ethyl acetate mixture

Sources & evidence

ORD record
ord-7ff52822615d4689b493026391f6a20a
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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