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

HRID 2383933Notes

Reaction equation

HRID 2383933 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.[CH3:23][N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]1.[OH-].[K+].C([O-])([O-])=O.[K+].[K+]>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:31][CH2:30][CH:27]4[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]4)[C:11]3=[O:22])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 2719711-Methyl-4-piperidinemethanolHCID 596362211-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 498727441-Benzothiazol-6-yl-3-[4-(1-methyl-piperidin-4-ylmethoxy)-pyridin-3-yl]-imidazolidin-2-oneYield 5.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one (I-180a: 150 mg, 0.4534 mmol) was reacted with (1-methyl-piperidin-4-yl)-methanol (88 mg, 0.6801 mmol), KOH (101 mg, 1.8138 mmol), K2CO3 (63 mg, 0.4534 mmol) and toluene (6 mL) to afford crude product. Purification by column chromatography on silica gel (10% MeOH in CHCl3), followed by preparative HPLC afforded 10 mg of the product (5% yield).

Workup

  1. customto afford crude product
  2. customPurification by column chromatography on silica gel (10% MeOH in CHCl3)

Sources & evidence

ORD record
ord-3f3bf73125c7465caf588436b0f3b7c2
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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