Hydrochloric Acid → (1-cyclohexyl-2-(5-(3-(methoxymethyl)phenyl)-1H-indazol-3-ylamino)-1H-benzo[d]imidazol-5-yl)methanol

HRID 2068293Notes

Reaction equation

HRID 2068293 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:10]=3[N:9]=[C:8]2[NH:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][O:35][CH3:36])[CH:29]=4)[CH:26]=3)[N:21](COCC[Si](C)(C)C)[N:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C(O)C>[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:10]=3[N:9]=[C:8]2[NH:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][O:35][CH3:36])[CH:29]=4)[CH:26]=3)[NH:21][N:20]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67253467(1-cyclohexyl-2-(5-(3-(methoxymethyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1H-benzo[d]imidazol-5-yl)methanol

Product 1

HCID 24798548(1-cyclohexyl-2-(5-(3-(methoxymethyl)phenyl)-1H-indazol-3-ylamino)-1H-benzo[d]imidazol-5-yl)methanolYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 20 mL vial with septum cover was added {1-cyclohexyl-2-[5-(3-methoxymethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-3-ylamino]-1H-benzoimidazol-5-yl}-methanol (58 mg, 0.000095 mol), ethanol (6.0 mL) and HCl (2.0 mL, 0.065 M). The mixture was refluxed for 1.5 hr. The mixture was concentrated and the residue dissolved in approx 1.5 mL of DMSO and purified by HPLC. The product fractions were lyopholized overnight to give 11.9 mg of the title compound as an off white solid.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hr
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue dissolved in approx 1.5 mL of DMSO
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-67d30d8955f643ebac3a69e0afba5200
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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