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 80083Notes

Reaction equation

HRID 80083 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 diethyl-ether. 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 diethyl-ether
  3. washThe precipitate was washed with ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b3657f2f60d345c5a6362a1aae7be101
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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