4-Chloro-2-methylphenyl isocyanate → HCID 11648354, Verbindung

HRID 736337

Reaktionsgleichung

Reaktionsgleichung von HRID 736337
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([CH3:11])[CH:3]=1.[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:25]=[N:26][CH:27]=[C:28]([NH2:30])[CH:29]=3)=[O:23])=[CH:20][N:19]([CH:31]([CH3:33])[CH3:32])[C:15]=2[N:16]=[CH:17][N:18]=1>N1C=CC=CC=1>[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:29]=[C:28]([NH:30][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=4[CH3:11])=[O:10])[CH:27]=[N:26][CH:25]=3)=[O:23])=[CH:20][N:19]([CH:31]([CH3:33])[CH3:32])[C:15]=2[N:16]=[CH:17][N:18]=1

Komponenten

4

Edukt 2

HCID 1421574-Chloro-2-methylphenyl isocyanateHCID 68903795HCID 68903795, Verbindung

Produkt 1

HCID 11648354HCID 11648354, VerbindungAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

4-Chloro-1-isocyanato-2-methyl-benzene (93.3 mg, 0.56 mmol) was added to a solution of (4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(5-amino-pyridin-3-yl)-methanone (150 mg, 0.51 mmol) in pyridine (5 mL). The mixture was heated to 45° C. for 12 h. The reaction mixture was concentrated in vacuo and the resulting yellow solid was triturated with CH2Cl2, filtered, and washed with CH2Cl2. Purification by flash column chromatography [(10% NH4OH/MeOH)/ethyl acetate 2:98] afforded the title compound as a white solid (197 mg, 83%). MS: 464.1 (MH+); HPLC Rf: 5.55 min. (HPLC method 4).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting yellow solid was triturated with CH2Cl2
  3. filtrationfiltered
  4. washwashed with CH2Cl2
  5. customPurification by flash column chromatography [(10% NH4OH/MeOH)/ethyl acetate 2:98]

Quellen und Nachweise

ORD-Eintrag
ord-2005108721c4467896be0ffb4794ac91
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595325B2

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