N-methyl-2-pyrrolidone → 7-Methoxy-N-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-4-phenylbenzo[d]thiazol-2-amine

HRID 451477Notes

Reaction equation

HRID 451477 reaction equation
Cl[C:2]1[S:3][C:4]2[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]=2[N:6]=1.Cl.Cl.[CH3:21][C:22]1[N:27]=[CH:26][N:25]=[C:24]([N:28]2[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]2)[CH:23]=1.CCN(C(C)C)C(C)C.CN1CCCC1=O>O1CCOCC1.O>[CH3:12][O:11][C:10]1[C:4]2[S:3][C:2]([NH:34][CH:31]3[CH2:32][CH2:33][N:28]([C:24]4[CH:23]=[C:22]([CH3:21])[N:27]=[CH:26][N:25]=4)[CH2:29][CH2:30]3)=[N:6][C:5]=2[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 673421331-(6-Methylpyrimidin-4-yl)piperidin-4-amine dihydrochlorideHCID 673440522-Chloro-7-methoxy-4-phenylbenzo[d]thiazole

Product 1

HCID 866567077-Methoxy-N-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-4-phenylbenzo[d]thiazol-2-amineYield 25.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
200 °C

Procedure

A solution of 2-chloro-7-methoxy-4-phenylbenzo[d]thiazole (100 mg, 363 μmol), 1-(6-methylpyrimidin-4-yl)piperidin-4-amine dihydrochloride (115 mg, 435 μmol) and Hunig's base (187 mg, 253 μL, 1.45 mmol) in dioxane (2 mL) was heated to 160° C. in a microwave oven for 30 minutes. N-Methyl-2-pyrrolidinone (0.5 mL) was added and the reaction was heated to 200° C. in a microwave oven for 2 hours. Water was added and the reaction was extracted twice with dichloromethane. The combined organic layers were washed with water and with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel using a gradient from dichloromethane to dichloromethane/methanol 9:1 (v/v) as eluent to yield the title compound as a light brown solid (40 mg, 25%). MS ISP (m/e): 432.4 (100) [(M+H)+].

Workup

  1. extractionthe reaction was extracted twice with dichloromethane
  2. washThe combined organic layers were washed with water and with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by column chromatography on silica gel using a gradient from dichloromethane to dichloromethane/methanol 9:1 (v/v) as eluent

Sources & evidence

ORD record
ord-fe8323675a854a37b89576521739436e
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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