Potassium Carbonate → Tert-butyl 4-(2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate

HRID 1429580Notes

Reaction equation

HRID 1429580 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:3][CH2:2]1.[Cl:30][C:31]1[CH:32]=[N:33][C:34](I)=[N:35][CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:30][C:31]1[CH:32]=[N:33][C:34]([N:1]2[CH2:6][CH2:5][CH:4]([O:7][C:8]3[S:9][C:10]4[CH:16]=[C:15]([CH:17]5[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]5)[CH:14]=[CH:13][C:11]=4[N:12]=3)[CH2:3][CH2:2]2)=[N:35][CH:36]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 299380055-Chloro-2-iodopyrimidineHCID 67465738Tert-butyl 4-(2-(piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate

Product 1

HCID 67467599Tert-butyl 4-(2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylateYield 31.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 4-(2-(piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate (337 mg, 0.807 mmol) and 5-chloro-2-iodopyrimidine (213 mg, 0.888 mmol) in DMF (10 mL) was added potassium carbonate (335 mg, 2.421 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was cooled to rt, diluted with water (30 mL), and extracted with EtOAc (3×10 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was recrystallized from EtOAc to afford tert-butyl 4-(2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate (133 mg, 0.251 mmol, 31% yield) as an off white solid. LCMS (m/z)=531 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-d697c20f80a74fd084a0690fff256bd5
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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