Potassium Carbonate → 1-Benzothiazol-6-yl-3-[4-(1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-3-yl]-imidazolidin-2-one

HRID 2383929Notes

Reaction equation

HRID 2383929 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][C:20]=4Cl)[C:11]3=[O:22])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[K+].C([O-])([O-])=O.[K+].[K+].[CH3:31][N:32]1[CH2:36][CH2:35][CH2:34][CH:33]1[CH2:37][OH:38]>C(Cl)(Cl)Cl.CO.C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][C:20]=4[O:38][CH2:37][CH:33]4[CH2:34][CH2:35][CH2:36][N:32]4[CH3:31])[C:11]3=[O:22])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 978361-Methyl-2-pyrrolidinemethanolHCID 596362211-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 498727411-Benzothiazol-6-yl-3-[4-(1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-3-yl]-imidazolidin-2-oneYield 5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

1-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one (I-180a: 100 mg, 0.3023 mmol) was added to a stirred mixture of KOH (68 mg, 1.2092 mmol), K2CO3 (42 mg, 0.3023 mmol) and toluene (3 mL) and the reaction mixture was stirred at RT for 5 mins. This was followed by the addition of (1-methyl-pyrrolidin-2-yl)-methanol (52 mg, 0.4534 mmol) and 18 crown ether (8 mg, 0.0302 mmol) and the resulting mixture was refluxed for 24 hrs. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated and the concentrate was partitioned between ethylacetate and water. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by preparative HPLC afforded 6 mg of the product (5% yield).

Workup

  1. temperaturethe resulting mixture was refluxed for 24 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe concentrate was partitioned between ethylacetate and water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-91f361a2bc13440badc7c2d2940cd488
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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