Methanol → HCID 49872837, compound

HRID 80253Notes

Reaction equation

HRID 80253 reaction equation
Cl.O1CCOCC1.[S:8]1[C:12]2[CH:13]=[C:14]([N:17]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=[C:24]5[CH:30]=[CH:29][N:28](COCC[Si](C)(C)C)[C:25]5=[N:26][CH:27]=4)[C:18]3=[O:39])[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1.CO.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[S:8]1[C:12]2[CH:13]=[C:14]([N:17]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=[C:24]5[CH:30]=[CH:29][NH:28][C:25]5=[N:26][CH:27]=4)[C:18]3=[O:39])[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 596361831-(benzothiazol-6-yl)-3-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrrolo [2,3-b]pyridin-5-yl)imidazolidin-2-one

Product 1

HCID 49872837HCID 49872837, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

1,4-Dioxane HCl (10 ml) was added to 1-(benzothiazol-6-yl)-3-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrrolo [2,3-b]pyridin-5-yl)imidazolidin-2-one (I-187b: 0.07 g, 0.19 mmol) and the resulting mixture was heated to 110° C. for 2 days. The reaction was monitored by TLC (20% MeOH in CHCl3). The reaction mixture was basified with Na2CO3 solution (pH˜8), cooled to room temperature, concentrated and the concentrate was washed with diethyl ether. Purification by preparative HPLC afforded 1.7 mg of the product (25.6% yield).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. washthe concentrate was washed with diethyl ether
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-79f3a31750d14d789423576556d22c07
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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