Trifluoroacetic acid → Trifluoroacetic acid

HRID 2383483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383483
C(OC([N:8]1[CH2:17][C:16]2[CH:15]=[N:14][C:13]3[NH:18][N:19]=[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH:28]C(OC(C)(C)C)=O)[CH:22]=4)[C:12]=3[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>ClCCl>[C:20]1([C:21]2[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=2)[CH2:27][NH2:28])[C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:17][C:16]=3[CH:15]=[N:14][C:13]=2[NH:18][N:19]=1.[C:38]([OH:40])([C:37]([F:42])([F:41])[F:36])=[O:39]

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 178453049HCID 178453049, Verbindung

Produkt 2

HCID 6422Trifluoroacetic acidHCID 178509726HCID 178509726, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-3,6,8,9-tetrahydro-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxylic acid tert-butyl ester (0.07 g, 0.14 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (1 mL). The mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and purified by reverse phase HPLC to give the desired product, 3-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-1-yl)-benzylamine as a bis TFA salt and as a white solid (0.046 g, 62%). 1H NMR (400 MHz, DMSO-d6) δ13.98 (s, 1H), 9.27 (brs, 2H), 8.45 (s, 1H), 8.30 (brs, 2H), 7.70 (s, 1H), 7.58 (m, 3H), 4.44 (s, 2H), 4.14 (m, 2H), 3.31 (m, 2H), 3.01 (m, 2H); LC-Mass: m/e 480.73 (M+H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1572987b663349e99a229b7ff63e181e
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263610B2

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