Trifluoroacetic acid → HCID 71290251, Verbindung

HRID 536494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536494
[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[C:16](I)[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)=[N:6]1.C(N(CC)C(C)C)(C)C.[C:40]([O:44][C:45](=[O:52])[NH:46][CH:47]1[CH2:51][CH2:50][NH:49][CH2:48]1)([CH3:43])([CH3:42])[CH3:41].FC(F)(F)C(O)=O>CN1CCCC1=O.O>[C:40]([O:44][C:45](=[O:52])[NH:46][CH:47]1[CH2:51][CH2:50][N:49]([C:16]2[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=[C:14]([C:7]3[C:8]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[N:5]([CH2:4][C:3]4[CH:27]=[CH:28][CH:29]=[CH:30][C:2]=4[F:1])[N:6]=3)[N:15]=2)[CH2:48]1)([CH3:43])([CH3:41])[CH3:42]

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 867053672-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Produkt 1

HCID 71290251HCID 71290251, VerbindungAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

150 mg (0.21 mmol, purity approx. 71%) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (example 15A) was dissolved, in a reaction vessel suitable for a microwave, in 1-methyl-2-pyrrolidone (3.1 ml), and 0.22 ml (1.24 mmol) of N,N-diisopropyl ethylamine and 154 mg (0.83 mmol) of tert.-butyl-pyrrolidin-3-ylcarbamate were added. Then the reaction vessel was sealed with a septum and was heated for 6 h at 150° C. in the microwave. After cooling, water was added to the reaction mixture, and trifluoroacetic acid extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and concentrated by evaporation. The residue was purified by preparative HPLC (acetonitrile:water (+0.1% trifluoroacetic acid) gradient). 69 mg of the title compound was obtained (59% of theor.).

Aufarbeitung

  1. customThen the reaction vessel was sealed with a septum
  2. temperatureAfter cooling
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue was purified by preparative HPLC (acetonitrile:water (+0.1% trifluoroacetic acid) gradient)

Quellen und Nachweise

ORD-Eintrag
ord-d7a48bb0d9d34771a7e79b860c3f653a
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859569B2

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