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Water → HCID 71285599, Verbindung

HRID 536530
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 536530
[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.Cl.Cl.[NH:42]1[CH2:45][CH:44]([N:46]2[CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:43]1.O>CN1CCCC1=O>[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]([N:42]3[CH2:45][CH:44]([N:46]4[CH2:50][CH2:49][CH2:48][CH2:47]4)[CH2:43]3)[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)=[N:6]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 19423677Pyrrolidine, 1-(3-azetidinyl)-, dihydrochlorideHCID 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 71285599HCID 71285599, VerbindungAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 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 1-methyl-2-pyrrolidone (3.1 ml) in a reaction vessel suitable for a microwave, and 0.29 ml (1.66 mmol) of N,N-diisopropyl ethylamine and 165 mg (0.83 mmol) of 1-(azetidin-3-yl)pyrrolidine-dihydrochloride were added. Then the reaction vessel was sealed with a septum and heated in the microwave at 150° C. for 6 h. After cooling, water was added to the reaction mixture. It was stirred for 30 min and filtered to remove the resultant solid. The filtrate was purified by preparative HPLC (acetonitrile:water (+0.1% trifluoroacetic acid) gradient). The product fraction was dissolved in dichloromethane and was washed twice with saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate, filtered and concentrated by evaporation. 52 mg of the title compound was obtained (46% of theor.; purity 94%).

Aufarbeitung

  1. additionwere added
  2. customThen the reaction vessel was sealed with a septum
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. customto remove the resultant solid
  6. customThe filtrate was purified by preparative HPLC (acetonitrile:water (+0.1% trifluoroacetic acid) gradient)
  7. dissolutionThe product fraction was dissolved in dichloromethane
  8. washwas washed twice with saturated aqueous sodium hydrogen carbonate solution
  9. dry with materialThe organic phase was dried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-fe19484c0e6d4d9198975c40a560dce6
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08859569B2

Notizen zur Reaktion

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