Water → HCID 53238990, compound

HRID 1966786Notes

Reaction equation

HRID 1966786 reaction equation
Cl.[CH3:2][NH:3]C.C[Al](C)C.C[O:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)=[C:14]([C:23]2[N:27]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]3[CH:32]=[CH:33][C:34]([C:36]4[CH:37]=[N:38][C:39]([NH2:42])=[N:40][CH:41]=4)=[CH:35][C:25]=3[N:24]=2)[CH:13]=1.O>C1(C)C=CC=CC=1>[NH2:42][C:39]1[N:38]=[CH:37][C:36]([C:34]2[CH:33]=[CH:32][C:26]3[N:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[C:23]([C:14]4[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=4[N:18]4[CH:22]=[N:21][CH:20]=[N:19]4)[C:11]([NH:3][CH3:2])=[O:10])=[N:24][C:25]=3[CH:35]=2)=[CH:41][N:40]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 16682925TrimethylaluminumHCID 53238989HCID 53238989, compound

Product 1

HCID 53238990HCID 53238990, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of dimethlyamine hydrochloride (20 mg, 0.3 mmol) in dry toluene (8 mL) is added AlMe3 (0.22 mL, 0.45 mmol) at room temperature. The solution is stirred at the same temperature for 15 minutes. 3-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzoimidazol-2-yl]-4-[1,2,4]triazol-1-yl-benzoic acid methyl ester (example 7) (70 mg, 0.15 mmol) is added to the solution and it is heated to 90° C. for 12 hours. The mixture is cooled down to room temperature and water (10 mL) is added. The mixture is extracted with EtOAc (3×10 mL) and the combined organic layer is dried by Mg2SO4 (300 mg) and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (17 mg, 25%). LCMS (ESMS): m/z 468.20 (M++1)

Workup

  1. temperatureThe mixture is cooled down to room temperature
  2. extractionThe mixture is extracted with EtOAc (3×10 mL)
  3. dry with materialthe combined organic layer is dried by Mg2SO4 (300 mg)
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-b2288c74137346beac0b4bd8a1ae7214
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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