Diisopropylethylamine → {4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-[1-(3-methyl-butyl)-piperidin-4-yl]-methanone

HRID 1069181노트

반응식

HRID 1069181 반응식
[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[CH:30]2[CH2:35][CH2:34][N:33]([C:11]([CH:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH:2]([CH3:1])[CH3:14])[CH2:10][CH2:9]3)=[O:13])[CH2:32][CH2:31]2)=[CH:25][CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10641624(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amineHCID 167689871-(3-Methylbutyl)piperidine-4-carboxylic acid

생성물 1

HCID 9958704{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-[1-(3-methyl-butyl)-piperidin-4-yl]-methanone수율 18%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

The preparation of Example 13: 1-(3-Methyl-butyl)-piperidine-4-carboxylic acid (0.1 g, 0.50 mmol) was dissolved in DMF (5 mL) and treated with (4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine (0.175 g, 0.50 mmol), diisopropylethylamine (0.26 mL, 1.5 mmol), and HBTU (0.19 g, 0.50 mmol). The reaction was stirred for 4 hours, then diluted with EtOAc (125 mL), washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 8% MeOH/CH2Cl2 to give 47 mg (18%) of {4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl }-[1-(3-methyl-butyl)-piperidin-4-yl]-methanone.

후처리

  1. customThe preparation of Example 13
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel eluting with 8% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-b7e4b4b82fd3437ca2865f199df2ef99
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251919B1

반응 노트

불러오는 중…