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

HRID 1069181ノート

反応式

HRID 1069181 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b7e4b4b82fd3437ca2865f199df2ef99
出典データセット
uspto-grants-2001_06
特許番号
US06251919B1

反応ノート

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