Triethylamine → (+)-4-{4-[3-(3-Benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile

HRID 2354561노트

반응식

HRID 2354561 반응식
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:19])[CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]3)=[CH:28][C:23]=2[O:22][CH2:21]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][N:32]([CH2:3][CH2:2][C:1]([N:5]4[CH2:6][CH2:7][N:8]([C:11]5[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:19])[CH:12]=5)[CH2:9][CH2:10]4)=[O:4])[CH2:31]3)=[CH:28][C:23]=2[O:22][CH2:21]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 170395273-Benzo[1,3]dioxol-5-ylmethyl-piperidineHCID 684518974-(4-Acryloylpiperazin-1-yl)-2-fluorobenzonitrile

생성물 1

HCID 12000651(+)-4-{4-[3-(3-Benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4-(4-acryloyl-piperazin-1-yl)-2-fluoro-benzonitrile (0.125 g, 0.48 mmol), (+)-3-benzo[1,3]dioxol-5-ylmethyl-piperidine (0.106 g, 0.48 mmol) and triethylamine (0.088 ml, 0.629 ml) in THF (1.6 ml) is stirred at rt for 25 h. The mixture is diluted with CH2Cl2 and washed with sat. aq. Na2CO3 solution The organic layer is separated off, dried over Na2SO4 and evaporated. The residue is purified by MPLC (60 g silica gel, eluent CH2Cl2:MeOH 9:1) to give the title compound, (+)-4-{4-[3-(3-benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile, as a colourless foam:

후처리

  1. washwashed with sat. aq. Na2CO3 solution The organic layer
  2. customis separated off
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue is purified by MPLC (60 g silica gel, eluent CH2Cl2:MeOH 9:1)

출처 및 근거

ORD 기록
ord-70f296480ab64e799f1e9dcefb154d27
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754719B2

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