Ammonium formate → HCID 178455392, compound

HRID 2289659Notes

Reaction equation

HRID 2289659 reaction equation
[CH3:1][Si:2]([CH3:36])([C:32]([CH3:35])([CH3:34])[CH3:33])[O:3][C@@H:4]([CH2:16][N:17](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:5][O:6][C:7]1[C:15]2[NH:14][CH:13]=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][Si:2]([CH3:36])([C:32]([CH3:34])([CH3:33])[CH3:35])[O:3][C@@H:4]([CH2:16][NH2:17])[CH2:5][O:6][C:7]1[C:15]2[NH:14][CH:13]=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178455393HCID 178455393, compound

Product 1

HCID 178455392HCID 178455392, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-4-[2-(Dimethyl-tert-butylsilyl)oxy-3-(dibenzylamino)propoxy]benzimidazole (1.27 g. 2.5 mmol) was dissolved in methanol (140 mL) and treated with an excess of ammonium formate (1.64 g, 25.0 mmol) followed by 10% palladium on carbon (410 mg). The resulting suspension was stirred at reflux for 1 hour. After cooling, the reaction mixture was filtered through a pad of celite. The filtrate was concentrated in vacuo to a brown oil (780 mg, 97%). NMR.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered through a pad of celite
  4. concentrationThe filtrate was concentrated in vacuo to a brown oil (780 mg, 97%)

Sources & evidence

ORD record
ord-f8cce3ee20324943ba0a36c6e0c7b474
Source dataset
uspto-grants-2000_07
Patent number
US06093735

Reaction notes

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