Diisopropylethylamine → (4-Methoxy-phenyl)-[5-(4-methoxy-phenyl)thiazol-2-yl]-amine

HRID 1713638

Reaktionsgleichung

Reaktionsgleichung von HRID 1713638
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22]CN4CCCC4)=[CH:17][CH:16]=3)=[N:11][CH:10]=2)=[CH:5][CH:4]=1.COC1C=CC(NC(N)=S)=CC=1.NC(N)=S.CCN(C(C)C)C(C)C>>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:12]2[S:13][C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:10][N:11]=2)=[CH:20][CH:19]=1

Komponenten

5

Edukt 4

HCID 81531DiisopropylethylamineHCID 6675494-ThioureidoanisoleHCID 2723790ThioureaHCID 11188635[5-(4-Methoxy-phenyl)-thiazol-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Produkt 1

HCID 11266955(4-Methoxy-phenyl)-[5-(4-methoxy-phenyl)thiazol-2-yl]-amine

Versuchsvorschrift

The title compound is prepared as described in Example 3 for [5-(4-methoxy-phenyl)-thiazol-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine but using (4-methoxy-phenyl)-thiourea. After addition of the thiourea and subsequent heating to reflux, the reaction mixture is allowed to cool to RT. DIEA (2.0 equiv) is added and the resulting mixture is heated to reflux for 70 min. Purification of the crude product by silica gel (40 g) column chromatography (CH2Cl2/Et2O, 95/5) affords the title compound as a beige solid: ES-MS: 312.9 [M+H]+; single peak at tR=7.66 min (System 1); Rf=0.11 (CH2Cl2/MeOH, 95/5).

Aufarbeitung

  1. customThe title compound is prepared
  2. temperaturesubsequent heating
  3. temperatureto reflux
  4. temperaturethe resulting mixture is heated
  5. temperatureto reflux for 70 min
  6. customPurification of the crude product by silica gel (40 g) column chromatography (CH2Cl2/Et2O, 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-334cbc4250d34130b05740b1826aca95
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795288B2

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