Trifluoroacetic acid → N-(3-(1H-benzo[d]imidazol-2-yl)-1H-indazol-5-yl)-1,4-dimethylpiperidine-4-carboxamide

HRID 1047538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047538
C(O)(C(F)(F)F)=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([C:29]3([CH3:36])[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[O:28])[CH:24]=2)[N:19](C2CCCCO2)[N:18]=1>C(Cl)Cl>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([C:29]3([CH3:36])[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[O:28])[CH:24]=2)[NH:19][N:18]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 136352251N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-1,4-dimethylpiperidine-4-carboxamide

Produkt 1

HCID 136232553N-(3-(1H-benzo[d]imidazol-2-yl)-1H-indazol-5-yl)-1,4-dimethylpiperidine-4-carboxamideAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (0.1 mL, 1.587 mmol) was added to a solution of N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-1,4-dimethylpiperidine-4-carboxamide (5 mg, 0.010 mmol) in CH2Cl2 (4 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Purification by flash chromatography (6% CH3OH/CH2Cl2) afforded the title compound (2 mg) as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.49 (bs, 1H), 7.64 (m, 4H), 7.29 (m, 2H), 3.49 (m, 2H), 3.18 (m, 2H), 2.91 (s, 3H), 2.59 (m, 2H), 1.46 (m, 2H), 1.28 (s, 3H); ESI-MS [M+H]+: 389.3.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customPurification by flash chromatography (6% CH3OH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e4f64ab512144be997ccb77e653ca3c7
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569511B2

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