Bicarbonate Ion → 1-Hydroxymethyl-3,3-dimethyl-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1,3-dihydro-indol-2-one

HRID 80191Notes

Reaction equation

HRID 80191 reaction equation
Cl.O1CCOCC1.[CH3:8][C:9]1([CH3:40])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N:18]3[CH2:22][CH2:21][N:20]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][C:28]=4[CH3:29])[C:19]3=[O:30])[CH:16]=2)[N:11]([CH2:31][O:32]CC[Si](C)(C)C)[C:10]1=[O:39].CO.C(=O)(O)[O-]>C(Cl)(Cl)Cl>[OH:32][CH2:31][N:11]1[C:12]2[C:17](=[CH:16][C:15]([N:18]3[CH2:22][CH2:21][N:20]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][C:28]=4[CH3:29])[C:19]3=[O:30])=[CH:14][CH:13]=2)[C:9]([CH3:8])([CH3:40])[C:10]1=[O:39]

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 687851223,3-Dimethyl-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indol-2-one

Product 1

HCID 596361741-Hydroxymethyl-3,3-dimethyl-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1,3-dihydro-indol-2-oneYield 94.87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dioxane HCl (4 mL) was added to 3,3-dimethyl-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indol-2-one (I-147a: 50 mg) and the resulting mixture was stirred room temperature for 1 hour. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was basified with bicarbonate solution and extracted with DCM. The organic layer was concentrated; the concentrate was recrystallized with DCM and hexane and dried to afford 37 mg of the product (94.87% yield).

Workup

  1. extractionextracted with DCM
  2. concentrationThe organic layer was concentrated
  3. customthe concentrate was recrystallized with DCM and hexane
  4. customdried

Sources & evidence

ORD record
ord-aff552bc84194a28a3522e5e8b66aebb
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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