Acetic Acid → HCID 17981674, compound

HRID 2252077Notes

Reaction equation

HRID 2252077 reaction equation
C=O.[CH:3]([S:6]([N:9]1[C:13]2[CH:14]=[C:15]([C:18]3[N:22]([CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:21]=[N:20][C:19]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH2:35])(=[O:8])=[O:7])([CH3:5])[CH3:4].[C:36](O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:3]([S:6]([N:9]1[C:13]2[CH:14]=[C:15]([C:18]3[N:22]([CH:23]4[CH2:28][CH2:27][N:26]([CH3:36])[CH2:25][CH2:24]4)[CH:21]=[N:20][C:19]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH2:35])(=[O:7])=[O:8])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 17981877HCID 17981877, compound

Product 1

HCID 17981674HCID 17981674, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add aqueous formaldehyde (37% w/w, 0.15 mmol) to a solution of 1-isopropylsulfonyl-2-amino-6-(1-(piperidin-4-yl)-4-(phenyl)-imidazol-5-yl)-benzimidazole (75 mg) in methanol (10 mL). Stir the mixture at room temperature for 30 minutes, then cool to 0° C. Add acetic acid (0.3 mL) followed by sodium cyanoborohydride (18 mg) and stir over night at room temperature. Concentrate the mixture under reduced pressure and then dissolve the residue in ethyl acetate. Wash the solution twice with 1 N sodium hydroxide and concentrate the organic phase under reduced pressure to provide 60 mg (79%) of the title compound. MS(ES+): m/z=479.6 (M+H)+

Workup

  1. temperaturecool to 0° C
  2. stirringstir over night at room temperature
  3. concentrationConcentrate the mixture under reduced pressure
  4. dissolutiondissolve the residue in ethyl acetate
  5. washWash the solution twice with 1 N sodium hydroxide
  6. concentrationconcentrate the organic phase under reduced pressure

Sources & evidence

ORD record
ord-abc5a12b221d4c1b9fd5edda0a8a75e2
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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