Diisopropylethylamine → (4-Benzyl-6-methyl-pyrimidin-2-yl)-[1-(3-chloro-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine

HRID 451435노트

반응식

HRID 451435 반응식
Cl.[CH2:2]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:23][C:24]1[N:28]=[C:27](Cl)[S:26][N:25]=1.C(N(CC)C(C)C)(C)C>O1CCCC1.O>[CH2:2]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:27]3[S:26][N:25]=[C:24]([Cl:23])[N:28]=3)[CH2:19][CH2:18]2)[N:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 2725055Dichloro-1,2,4-thiadiazoleHCID 67344140(4-Benzyl-6-methyl-pyrimidin-2-yl)-piperidin-4-yl-amine hydrochloride

생성물 1

HCID 53353526(4-Benzyl-6-methyl-pyrimidin-2-yl)-[1-(3-chloro-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (4-benzyl-6-methyl-pyrimidin-2-yl)-piperidin-4-yl-amine hydrochloride (159 mg, 0.5 mmol), 3,5-dichloro-[1,2,4]thiadiazol (39 mg, 0.25 mmol) and N,N-diisopropylethylamine (85 L, 0.5 mmol) in tetrahydrofurane (2 mL) was heated to 95° C. 4 hours under nitrogen. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using Et2O as eluent. The title compound was obtained as a colorless oil (52 mg, 52%).

후처리

  1. custom4 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-28760e8c971047d4b42f8539e7f09ff5
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

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