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Acetic Acid → HCID 178428324, Verbindung

HRID 2046975
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2046975
[CH:1]([O:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:8]([CH3:17])=[CH:7][C:6]=1[NH:18][C:19]1[N:24]=[C:23]2[NH:25][N:26]=[C:27]([CH3:28])[C:22]2=[C:21]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[N:20]=1)([CH3:3])[CH3:2].[CH3:42]C(O)=O.C=O.[NH4+].[Cl-]>CO.C1COCC1>[CH:1]([O:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:42])[CH2:13][CH2:12]2)[C:8]([CH3:17])=[CH:7][C:6]=1[NH:18][C:19]1[N:24]=[C:23]2[NH:25][N:26]=[C:27]([CH3:28])[C:22]2=[C:21]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[N:20]=1)([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 178428323HCID 178428323, Verbindung

Produkt 1

HCID 178428324HCID 178428324, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887Methanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N6-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (39 mg, 0.067 mmol) in 5.0 mL of MeOH and 5.0 mL of THF was added drops of AcOH and HCHO [1N in MeOH and THF (v/v: 1/1), 0.12 mmol, 120 μL] sequentially. The reaction mixture was stirred at room temperature for 30 min, then NaB(CN)H3 (6.6 mg, 0.12 mmol) was added and the reaction mixture was stirred for another 1 h. Saturated aqueous NH4Cl was added to the reaction and the reaction mixture was concentrated in vacuo. The crude was partitioned between EtOAc and brine. The organic extracts were concentrated and purified by RP-HPLC to afford N6-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine. MS (ES+): 592.3 (MH+).

Aufarbeitung

  1. additionNaB(CN)H3 (6.6 mg, 0.12 mmol) was added
  2. stirringthe reaction mixture was stirred for another 1 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe crude was partitioned between EtOAc and brine
  5. concentrationThe organic extracts were concentrated
  6. custompurified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-990582ddeb134f7d8d2069c76e809672
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592432B2

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