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

HRID 451401

반응식

HRID 451401 반응식
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

참가 물질

7

반응물 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

생성물 1

HCID 58397898HCID 58397898, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b5a8904add3e45839fa2c47615c53cbf
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

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