N-methyl-2-pyrrolidone → HCID 58397898, compound

HRID 451401Notes

Reaction equation

HRID 451401 reaction equation
Cl.Cl.[C:3]1([CH:9]2[C:14]3[N:15]=[C:16]([NH:18][CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[S:17][C:13]=3[CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:35]1[CH:40]=[C:39]([CH3:41])[N:38]=[CH:37][N:36]=1.CN1CCCC1=O>O1CCCC1.O>[CH3:41][C:39]1[N:38]=[CH:37][N:36]=[C:35]([N:22]2[CH2:21][CH2:20][CH:19]([NH:18][C:16]3[S:17][C:13]4[CH2:12][CH2:11][CH2:10][CH:9]([C:3]5[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=5)[C:14]=4[N:15]=3)[CH2:24][CH2:23]2)[CH:40]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 5817964-Chloro-6-methylpyrimidineHCID 86656698(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-piperidin-4-yl-amine dihydrochloride

Product 1

HCID 58397898HCID 58397898, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-piperidin-4-yl-amine dihydrochloride (77.3 mg, 0.2 mmol) was suspended in tetrahydrofurane (2 mL). At 0° C. N,N-diisopropylethylamine (110 1, 0.64 mmol) was added at room temperature under nitrogen and stirring. To the yellow solution 4-chloro-6-methylpyrimidine (28.9 mg, 0.22 mmol) was added and the reaction was stirred at room temperature over night. The reaction was heated to reflux over night and then heated with N-methylpyrrolidone in a microwave oven to 200° C. for 30 minutes. Water was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient from EtOAc to EtOAc/EtOH 9:1 (v/v) as eluent. The title compound was obtained as a light yellow solid (55 mg, 68%).

Workup

  1. customAt 0° C
  2. stirringthe reaction was stirred at room temperature over night
  3. temperatureThe reaction was heated
  4. temperatureto reflux over night
  5. extractionthe reaction was extracted twice with diethyl ether
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel using a gradient from EtOAc to EtOAc/EtOH 9:1 (v/v) as eluent

Sources & evidence

ORD record
ord-b5a8904add3e45839fa2c47615c53cbf
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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