Water → (S)-1-(4-fluoro-benzenesulfonyl)-piperidine-2-carboxylic acid[2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-amide

HRID 1051231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051231
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([NH2:19])[CH:13]=2.[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]2[C:36](O)=[O:37])(=[O:29])=[O:28])=[CH:23][CH:22]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([NH:19][C:36]([C@@H:31]1[CH2:32][CH2:33][CH2:34][CH2:35][N:30]1[S:27]([C:24]1[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=1)(=[O:29])=[O:28])=[O:37])[CH:13]=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 768662(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 901028912-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-ylamine

Produkt 1

HCID 74220673(S)-1-(4-fluoro-benzenesulfonyl)-piperidine-2-carboxylic acid[2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-amideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-ylamine (35 mg, 0.13 mmol) in CH2Cl2 (5 mL) was added (S)-1-(4-fluoro-benzenesulfonyl)-piperidine-2-carboxylic acid (37 mg, 0.13 mmol) and HATU (49 mg, 0.13 mol). The solution was stirred at 25° C. for 1 h and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded (S)-1-(4-fluoro-benzenesulfonyl)-piperidine-2-carboxylic acid[2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-amide (60 mg, 86%) as a white solid. MH+ 543.0.

Aufarbeitung

  1. extractionThe aqueous phase was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration
  5. concentrationfollowed by concentration in vacuo
  6. customgave a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-0552468db34f425d8c0965b4981a2a11
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388166B2

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