Trifluoroacetic acid → 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide

HRID 468463노트

반응식

HRID 468463 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH:25]([CH2:28][OH:29])[CH2:26][OH:27])[CH:20]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.FC(F)(F)C(O)=O.ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH:25]([CH2:26][OH:27])[CH2:28][OH:29])[C:20]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 8371ChloranilHCID 591294261-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)indolin-5-yl)cyclopropanecarboxamide

생성물 1

HCID 591292921-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

1-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)indolin-5-yl)cyclopropanecarboxamide (40.3 mg, 0.0711 mmol as the trifluoracetic acid salt) was dissolved in toluene (1 mL). To the resulting solution was added 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione (35 mg, 0.14 mmol). The resulting suspension was heated at 100 CC in an oil bath for 10 minutes. The crude product was then evaporated to dryness, dissolved in a 1 mL of NA-dimethylformamide and purified by purified by preparative HPLC using a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)-1H-indol-5-yl)cyclopropanecarbox amide. ESI-MS m/z calc. 450.2, found 451.5 (M+1)+. Retention time of 1.59 minutes.

후처리

  1. temperatureThe resulting suspension was heated at 100 CC in an oil bath for 10 minutes
  2. customThe crude product was then evaporated to dryness
  3. dissolutiondissolved in a 1 mL of NA-dimethylformamide
  4. custompurified
  5. customby purified by preparative HPLC

출처 및 근거

ORD 기록
ord-91638bed8e7544c7bfc6f8553d670f90
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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