Methanol → 1-(1H-indazol-5-yl)-3-(4-methylpyridin-3-yl)imidazolidin-2-one

HRID 80052Notes

Reaction equation

HRID 80052 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N:15]1[CH2:19][CH2:18][N:17]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25](COCC[Si](C)(C)C)[N:24]=[CH:23]3)[C:16]1=[O:37].CO>C(Cl)Cl.C(Cl)(Cl)Cl>[NH:25]1[C:26]2[C:22](=[CH:21][C:20]([N:17]3[CH2:18][CH2:19][N:15]([C:10]4[CH:11]=[N:12][CH:13]=[CH:14][C:9]=4[CH3:8])[C:16]3=[O:37])=[CH:28][CH:27]=2)[CH:23]=[N:24]1

Participants

6

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 687857481-(4-Methyl-pyridin-3-yl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-imidazolidin-2-one

Product 1

HCID 498719661-(1H-indazol-5-yl)-3-(4-methylpyridin-3-yl)imidazolidin-2-oneYield 25.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (0.096 g, 0.00084 mol) was added to solution of 1-(4-methyl-pyridin-3-yl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-imidazolidin-2-one (0.24 g, 0.00056 mol) in DCM (10 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated and the concentrate was purified by preparative HPLC to afford 42 mg of the product (19.47% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe concentrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-59f06296de6148919d5c20b7c60cfaee
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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