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Diisopropylethylamine → 4-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3-fluoro-piperidin-1-yl)-ethyl]-piperidin-4-yl}-amide

HRID 1929221
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HRID 1929221 반응식
[N:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16]([C:18]3[NH:19][C:20]4[C:25]([CH:26]=3)=[C:24]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:23]=[CH:22][CH:21]=4)=[O:17])[CH2:11][CH2:10]2)[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.Cl.[F:33]C1CCCNC1.CCN(C(C)C)C(C)C.[I-].C(C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#N>C(#N)CC.CCOC(C)=O>[F:33][CH:5]1[CH2:4][CH2:3][CH2:2][N:1]([CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([NH:15][C:16]([C:18]3[NH:19][C:20]4[C:25]([CH:26]=3)=[C:24]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:23]=[CH:22][CH:21]=4)=[O:17])[CH2:13][CH2:14]2)[CH2:6]1
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참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 27591563-FLUOROPIPERIDINE HYDROCHLORIDEHCID 589163264-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3,6-dihydro-2h-pyridin-1-yl)-ethyl]-piperidin-4-yl}-amideHCID 87175442Cyanomethyl-triphenyl phosphonium iodide

생성물 1

HCID 596001974-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3-fluoro-piperidin-1-yl)-ethyl]-piperidin-4-yl}-amide

시약·촉매·용매 2

HCID 7854Propionitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

To a suspension of 190 (see example 150) (100 mg, 0.28 mmol), 3-fluoropiperidine hydrochloride (43 mg, 0.208 mmol) and DIEA (0.189 ml, 1.12 mmol) in 0.5 ml of propionitrile is added cyanomethyl-triphenyl phosphonium iodide (81 mg, 0.336 mmol). The mixture is heated at 90° C. for 14 hours. The resulting solution is then diluted with EtOAc (20 ml) and washed twice with saturated sodium bicarbonate, dried over sodium sulfate and evaporated. The crude product is further purified by preparative HPLC.

후처리

  1. washwashed twice with saturated sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe crude product is further purified by preparative HPLC

출처 및 근거

ORD 기록
ord-65dcf333f78c4dd0b08b47696bc29889
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183366B2

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