Sodium cyanoborohydride → 5-bromo-1-methyl-3-(5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-one

HRID 592624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592624
BrC1C=C(NC2C=CC([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][O:25][CH2:24]4)[CH2:19][CH2:18]3)=CN=2)C(=O)N(C)C=1.[Br:27][C:28]1[CH:29]=[C:30]([NH:36][C:37]2[CH:45]=C3CNCCN3[N:38]=2)[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=1.O1CC(=O)C1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-].C(Cl)Cl.C(OCC)C.CO>[Br:27][C:28]1[CH:29]=[C:30]([NH:36][C:37]2[CH:45]=[C:22]3[CH2:21][N:20]([CH:23]4[CH2:24][O:25][CH2:26]4)[CH2:19][CH2:18][N:17]3[N:38]=2)[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=1

Komponenten

8

Edukt 4

HCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 580437855-Bromo-1-methyl-3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-oneHCID 580437945-Bromo-1-methyl-3-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one

Produkt 1

HCID 580441695-bromo-1-methyl-3-(5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-oneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel2×HCID 22565053DCM ether MeOHLösungsmittel

Reaktionsbedingungen

Temperatur
48 °C

Versuchsvorschrift

Compound 125i was synthesized using the same procedure as 101k, where 5-bromo-1-methyl-3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-one (125h) (250 mg, 0.78 mmol), and oxetan-3-one (600 mg, 8.3 mmol) in methanol (8 mL) were mixed. Sodium cyanoborohydride (148 mg, 3 mmol) and zinc chloride (165 mg, 1.5 mmol) in methanol (8 mL) was added, and the reaction was heated at 48° C. for 12 hours. Work-up and flash column chromatography (silica, 60:35:5 methylene chloride/diethyl ether/methanol) afford a 34% yield (100 mg) of 5-bromo-1-methyl-3-(5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-one (125i) as a light green solid: MS (ESI+) m/z 382.1 (M+H).

Aufarbeitung

  1. customCompound 125i was synthesized
  2. additionwere mixed

Quellen und Nachweise

ORD-Eintrag
ord-8d557182ba254667af279e15f32de122
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238655B2

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