Diisopropylethylamine → [1-(3-Methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 451403

반응식

HRID 451403 반응식
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.Cl.Cl.[C:28]1([CH:34]2[C:39]3[N:40]=[C:41]([NH:43][CH:44]4[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]4)[S:42][C:38]=3[CH2:37][CH2:36][CH2:35]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)C(C)C)(C)C.Cl[C:60]1[S:64][N:63]=[C:62]([CH3:65])[N:61]=1>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:65][C:62]1[N:61]=[C:60]([N:47]2[CH2:46][CH2:45][CH:44]([NH:43][C:41]3[S:42][C:38]4[CH2:37][CH2:36][CH2:35][CH:34]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:39]=4[N:40]=3)[CH2:49][CH2:48]2)[S:64][N:63]=1

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 129191595-Chloro-3-methyl-1,2,4-thiadiazoleHCID 86656698(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-piperidin-4-yl-amine dihydrochloride

생성물 1

HCID 53354635[1-(3-Methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
200 °C

실험 절차

Palladium (II) acetate (3.6 mg, 0.016 mmol) and 2-(dicyclohexylphosphino)biphenyl (11.6 mg, 0.032 mmol) were stirred under nitrogen at room temperature in dioxane (1.8 mL) for 10 minutes. Sodium tert.-butylat (29 mg, 0.3 mmol), (4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-piperidin-4-yl-amine dihydrochloride (77.3 mg, 0.2 mmol), N,N-diisopropylethylamine (69 L, 0.4 mmol) and 5-chloro-3-methyl-[1,2,4]thiadiazole (29.6 mg; 0.22 mmol) were added and the reaction was heated to 200° C. for 30 minutes in a microwave oven. The reaction was diluted with water and extracted twice with ethyl acetate. 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 heptane/EtOAc 4:1 to 1:4 (v/v) as eluent. The title compound was obtained as a white solid (55 mg, 67%).

후처리

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-128b987ab884452eb996b211b380ab22
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

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