Ammonium Chloride → HCID 53239212, compound

HRID 1966787Notes

Reaction equation

HRID 1966787 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=2[C:18]2[N:22]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]3[CH:27]=[CH:28][C:29]([C:31]4[CH:32]=[N:33][C:34]([NH2:37])=[N:35][CH:36]=4)=[CH:30][C:20]=3[N:19]=2)[N:6]=1)=[O:4].[H-].[CH2:39]([Al+]CC(C)C)[CH:40](C)[CH3:41].[NH4+].[Cl-]>C1COCC1>[CH2:1]([O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=2[C:18]2[N:22]([C:23]([CH3:26])([CH3:24])[CH3:25])[C:21]3[CH:27]=[CH:28][C:29]([C:31]4[CH:36]=[N:35][C:34]([NH2:37])=[N:33][CH:32]=4)=[CH:30][C:20]=3[N:19]=2)[N:6]=1)=[O:4])[CH:40]([CH3:41])[CH3:39]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 53238992HCID 53238992, compound

Product 1

HCID 53239212HCID 53239212, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{2-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzoimidazol-2-yl]-4-cyano-phenyl}-1H-[1,2,4]triazole-3-carboxylic acid methyl ester (example 64) (100 mg, 0.2 mmol) in dry THF (10 mL) is added Diisobutyl aluminium hydride (DIBALH) (1 M THF solution) (0.4 mL, 0.4 mmol) at 0° C. under nitrogen atmosphere. The solution is warmed to room temperature for 24 hours. Sat. NH4Cl solution (10 mL) is added and the mixture is extracted with EtOAc (3×10 mL). The combined organic layer is dried with Mg2SO4 (500 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 (29 mg, 26%). LCMS (ESMS): m/z 536.40 (M++1)

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL)
  2. dry with materialThe combined organic layer is dried with Mg2SO4 (500 mg)
  3. filtrationis filtered
  4. concentrationThe filtrate is concentrated
  5. customthe residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-f1f8049d1a09424eb6861a9e347af687
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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