Diisopropylethylamine → HCID 86694721, Verbindung

HRID 475185

Reaktionsgleichung

Reaktionsgleichung von HRID 475185
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[S:17]([N:27]1[C:35]2[C:30](=[C:31]([CH2:36][NH2:37])[CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28]1)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].CCN(C(C)C)C(C)C>CC(O)C>[CH:14]1([C:11]2[NH:12][N:13]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:37][CH2:36][C:31]4[CH:32]=[CH:33][CH:34]=[C:35]5[C:30]=4[CH:29]=[CH:28][N:27]5[S:17]([C:20]4[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=4)(=[O:19])=[O:18])[N:7]=3)[CH:10]=2)[CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 67262154(1-Tosyl-1H-indol-4-YL)methanamineHCID 178478345HCID 178478345, Verbindung

Produkt 1

HCID 86694721HCID 86694721, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A tube was charged with 53 (415 mg, 1.38 mmol), 46 (486 mg, 2.07 mmol), DIPEA (1.0 ml) and IPA (3 mL), degassed, sealed and heated at 120° C. overnight. The mixture was concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (3.3 to 5% MeOH) to afford 330 mg (48%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-indol-4-yl)methyl)pyrimidine-2,4-diamine (50) as yellow solid: MS (ESI) m/z=500.3 [M+1]+.

Aufarbeitung

  1. customdegassed
  2. customsealed
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was purified by SiO2 chromatography
  5. washeluting with a DCM/MeOH gradient (3.3 to 5% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-fd6e96044cdd4da290e06e6e4939793b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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