Water → HCID 58541891, compound

HRID 1966767Notes

Reaction equation

HRID 1966767 reaction equation
[OH-].[NH4+:2].[C:3]([N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:17]=[N:18][C:19]([NH2:22])=[N:20][CH:21]=3)=[CH:15][C:10]=2[N:9]=[C:8]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:33]=[C:32](C(Cl)(Cl)Cl)[O:31][N:30]=1)([CH3:6])([CH3:5])[CH3:4].O>CN(C=O)C>[NH2:2][C:32]1[O:31][N:30]=[C:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:8]2[N:7]([C:3]([CH3:5])([CH3:6])[CH3:4])[C:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:17]=[N:18][C:19]([NH2:22])=[N:20][CH:21]=4)=[CH:15][C:10]=3[N:9]=2)[N:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 58542015HCID 58542015, compound

Product 1

HCID 58541891HCID 58541891, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ammonium hydroxide (0.02 mL, 0.39 mmol) in DMF (2 mL) at room temperature is added 5-{1-tert-butyl-2-[2-(5-trichloromethyl-[1,2,4]oxadiazol-3-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine (395 mg, 0.26 mmol). The reaction mixture is stirred at room temperature for 0.5 hours. Water is added to the reaction mixture and the product is extracted into EtOAc (3×) and the combined organics are then dried (Na2SO4), filtered, and concentrated. Purification via flash chromatography (10 g silica gel, 3-6% MeOH/CH2Cl2) affords the title compound (20.6 mg, 17%). LCMS (ESMS): m/z 427.29 (M++1)

Workup

  1. extractionthe product is extracted into EtOAc (3×)
  2. dry with materialthe combined organics are then dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography (10 g silica gel, 3-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-047fd67bfa0e4614beefd80abe1acc23
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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