Lithium Hexamethyldisilazide → N5-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-6-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine

HRID 1042279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042279
F[C:2]1[C:7]([C:8]2[N:13]=[CH:12][N:11]=[C:10]3[NH:14][N:15]=[CH:16][C:9]=23)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:17][C:18]1[CH:27]=[CH:26][C:25]2[C:24]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)=[N:23][CH:22]=[CH:21][C:20]=2[C:19]=1[NH2:39].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].N.CO>C1COCC1.CC(O)=O.CO>[NH:14]1[C:10]2=[N:11][CH:12]=[N:13][C:8]([C:7]3[C:2]([NH:39][C:19]4[C:20]5[CH:21]=[CH:22][N:23]=[C:24]([NH:28][C:29]6[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:36])[F:37])[CH:30]=6)[C:25]=5[CH:26]=[CH:27][C:18]=4[CH3:17])=[N:3][CH:4]=[CH:5][CH:6]=3)=[C:9]2[CH:16]=[N:15]1

Komponenten

8

Edukt 4

HCID 2733832Lithium HexamethyldisilazideHCID 21705897Ammonia methanolHCID 444789036-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamineHCID 596273834-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 59627374N5-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-6-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (30 mg, 139 μmol) and 6-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine (49 mg, 153 μmol) in THF (3 mL) was treated with lithium bis(trimethylsilyl)amide (1.0 M solution in THF; 627 μL, 627 μmol). The mixture was stirred at it for 3 h and then heated in a microwave at 100° C. for 20 min. The mixture was poured into MeOH (15 mL) and AcOH (0.5 mL) and then 2M NH3/MeOH (30 mL) was added. Solvent was removed in vacuo. The product was purified by flash chromatography eluting with MeOH/DCM (1-5%) to give N5-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-6-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine. MS (ESI, pos. ion) m/z: 513.2 [M+H]+

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. customThe product was purified by flash chromatography
  3. washeluting with MeOH/DCM (1-5%)

Quellen und Nachweise

ORD-Eintrag
ord-a42f435d804941c493cca516a3753c8a
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557830B2

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