1,2-Dichloroethane → 5-[4-(5-Amino-3-tert-butyl-pyrazol-1-yl)-phenyl]-morpholin-4-yl-methanone

HRID 1661004

Reaktionsgleichung

Reaktionsgleichung von HRID 1661004
[NH2:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=O)=[CH:9][CH:8]=2)[N:5]=[C:4]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(Cl)CCl.C1C[O:33]CC1>>[NH2:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][C:10]([CH:11]3[N:20]([CH:25]=[O:33])[CH2:21][CH2:22][O:23][CH2:24]3)=[CH:9][CH:8]=2)[N:5]=[C:4]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1

Komponenten

5

Edukt 4

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 8083MorpholineHCID 9746884-(5-Amino-3-tert-butyl-pyrazol-1-yl)-benzoic acid

Produkt 1

HCID 866258265-[4-(5-Amino-3-tert-butyl-pyrazol-1-yl)-phenyl]-morpholin-4-yl-methanone

Versuchsvorschrift

To a solution of 515 mg (1.98 mmol) 4-(5-amino-3-tert-butyl-pyrazol-1-yl)-benzoic acid and 259 μL (2.98 mMol) morpholine in 8 mL THF, 495 mg (2.58 mmol) of EDC are added at rt. The reaction is stirred at rt for 2 h. After completion, the resulting reaction mixture is concentrated and the residue is taken up in CH2Cl2, washed with brine (2×), dried and concentrated. The residual crude product is purified by flash chromatography (SiO2, CH2Cl2/MeOH; gradient 0-5% MeOH) to give the title compound as an off white powder. MS: [M+1]+=329.

Aufarbeitung

  1. customAfter completion, the resulting reaction mixture
  2. concentrationis concentrated
  3. washwashed with brine (2×)
  4. customdried
  5. concentrationconcentrated
  6. customThe residual crude product is purified by flash chromatography (SiO2, CH2Cl2/MeOH; gradient 0-5% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-8e7f78ea5e4b409cb5ef990d2f22fd7b
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030311B2

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