7-Chlorothieno[3,2-b]pyridine-2-carboxylic acid → HCID 22603606, Verbindung

HRID 2308092

Reaktionsgleichung

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[S:10][C:3]=12.[CH3:14][NH:15][C:16]([N:18]1[C:26]2[C:21](=[CH:22][C:23]([NH2:27])=[CH:24][CH:25]=2)[CH:20]=[C:19]1[CH3:28])=[O:17]>CS(C)=O>[CH3:28][C:19]1[N:18]([C:16](=[O:17])[NH:15][CH3:14])[C:26]2[C:21]([CH:20]=1)=[CH:22][C:23]([NH:27][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[S:10][C:3]=13)=[CH:24][CH:25]=2

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

To 0.68 g (1.23 mmol) of 7-Chloro-thieno[3,2-b]pyridine-2-carboxylic acid, prepared as described in Groton patent, was added 0.25 g (1.23 mmol) of 5-Amino-2-methyl-indole-1-carboxylic acid methylamide, prepared as described in Example 1(a) steps (i) to (iii), dissolved in 3 mL of DMSO that was degassed with Ar and warmed to 75° C. The solution was stirred for 14 h, cooled to 25° C. and filtered. The precipitate was rinsed with EtOAc (2×5 mL) and put under high vacuum for 12 h to give 0.43 g (98%) of 7-(2-Methyl-1-methylcarbamoyl-1H-indol-5-ylamino)-thieno[3,2-b]pyridine-2-carboxylic acid as yellow solid. HPLC: Rt 3.38 min. (97.2% area). 1H NMR (CDCl3, 300 MHz) δ 9.18 (1H, bs), 8.37 (1H, d, J=5.6 Hz), 8.30 (1H, q, J=3.4 Hz), 7.94 (1H, s), 7.70 (1H, d, J=8.7 Hz), 7.46 (1H, s), 7.17 (1H, dd, J=8.8, 1.9 Hz), 6.79 (1H, d, J=5.6 Hz), 6.45 (1H, s), 2.96 (3H, s), 2.94 (3H, s). LCMS (APCI) (M+H+) m/z: 381.1

Aufarbeitung

customprepared
customwas degassed with Ar
temperaturecooled to 25° C.
filtrationfiltered
washThe precipitate was rinsed with EtOAc (2×5 mL)
waitput under high vacuum for 12 h

Quellen und Nachweise

ORD-Eintrag: ord-8a5f67eaaf2347719966b556b0f5eaaa
Quelldatensatz: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06833456B2

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