Triethylamine → N-(3,4-Difluorobenzyl)-2-(4,5-dihydrooxazol-2-yl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

HRID 40105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40105
[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[C:29]([NH:31][CH2:32][CH2:33]O)=[O:30])=[O:8].CCN(CC)CC.CS(Cl)(=O)=O>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[C:29]1[O:30][CH2:33][CH2:32][N:31]=1)=[O:8]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59762352HCID 59762352, Verbindung2×

Produkt 1

HCID 59762390N-(3,4-Difluorobenzyl)-2-(4,5-dihydrooxazol-2-yl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N3-(3,4-difluorobenzyl)-N2-(2-hydroxyethyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-2,3-dicarboxamide (Compound 103, 36 mg, 0.069 mmol) in CH2Cl2 (3 ml) at 0° C was added Et3N (58 μl, 0.41 mmol) and methanesulfonyl chloride (11 μl, 0.14 mmol). The reaction was stirred at room temperature for 0.5 h, diluted with EtOAc, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound as a yellow film.

Aufarbeitung

  1. washwashed with H2O and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-eb798b0bc03a4c07963b33145689dc4e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524917B2

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