Hydrochloric Acid → 1-(4-Methyl-pyridin-3-yl)-3-(4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-imidazolidin-2-one, hydrochloride

HRID 2383767Notes

Reaction equation

HRID 2383767 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([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])[S:17][C:11]=2[CH2:10]1)=O)(C)(C)C>CO.C(Cl)Cl>[ClH:1].[CH3:29][C:28]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1[N:20]1[CH2:21][CH2:22][N:18]([C:16]2[S:17][C:11]3[CH2:10][NH:9][CH2:14][CH2:13][C:12]=3[CH:15]=2)[C:19]1=[O:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 687887812-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester

Product 1

HCID 1317299401-(4-Methyl-pyridin-3-yl)-3-(4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-imidazolidin-2-one, hydrochlorideYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

6N HCl (5 mL) was added dropwise to stirred solution of 2-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester (70 mg, 0.16887 mmol) in methanol (2 mL) at 0° C. The reaction mixture was stirred at room temperature for 12 hours. The reaction was monitored by TLC (5% MeOH in DCM). The solvent was distilled from the reaction mixture under reduced pressure, followed by the addition of diethylether. The precipitate was washed with ether and dried under reduced pressure to afford 36 mg of the product (61% yield).

Workup

  1. distillationThe solvent was distilled from the reaction mixture under reduced pressure
  2. additionfollowed by the addition of diethylether
  3. washThe precipitate was washed with ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-de658459503a4b2d8c6a1675c0742caf
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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