Trifluoroacetic acid → HCID 44622554, Verbindung

HRID 42359

Reaktionsgleichung

Cl[C:2]1[N:3]=[C:4]([NH:19][C:20]2([C:23]([F:26])([F:25])[F:24])[CH2:22][CH2:21]2)[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.Cl.[NH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1.C(N(C(C)C)CC)(C)C.C(O)(C(F)(F)F)=O>CN1C(=O)CCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:2]([NH:28][CH2:29][C:30]4[CH:31]=[CH:32][C:33]([S:36]([NH2:39])(=[O:37])=[O:38])=[CH:34][CH:35]=4)[N:3]=[C:4]([NH:19][C:20]4([C:23]([F:26])([F:25])[F:24])[CH2:22][CH2:21]4)[C:5]=3[N:11]=2)=[CH:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

A mixture of [2-Chloro-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-4-yl]-(1-trifluoromethyl-cyclopropyl)-amine (51.6 mg) and 4-aminomethyl-benzenesulfonamide hydrochloride (51.4 mg) was dissolved in NMP (1 mL) and treated with diisopropylethylamine (0.065 mL). The reaction mixture was sealed and heated by microwave to 140° C. for 1.5 h. The reaction mixture was cooled and purified by preparative HPLC (5-95% acetonitrile:water with 0.1% TFA) to afford 36 mg (41% yield) of the title compound as its TFA which was characterized by its NMR and mass spectrum as follows: 1H NMR (d6-DMSO): d 1.26 (br s, 2H), 1.37 (br s, 2H), 4.80 (d, 2H), 7.34-7.40 (m, 4H), 7.55 (d, 2H), 7.78 (d, 2H), 7.99 (d, 1H), 8.48 (m, 3H), 8.9 (br s, 1H), 10.1 (br s, 1H); MS (m/z): 533.2 ([M+H]+, 100).

Aufarbeitung

customThe reaction mixture was sealed
temperatureThe reaction mixture was cooled
custompurified by preparative HPLC (5-95% acetonitrile:water with 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag: ord-9e3b2b283d9c441bb17f011cd5d90186
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536187B2

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