1,2-Dichloroethane → HCID 178454346, Verbindung

HRID 1875182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875182
[NH2:1][CH2:2][C:3]1[C:4]([F:22])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([CH:19]3[CH2:21][CH2:20]3)[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[CH3:23][C:24]([O:27][C:28]([N:30]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:31]1[NH:32][C:33]([C:37](O)=[O:38])=[C:34]([Cl:36])[N:35]=1)=[O:29])([CH3:26])[CH3:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH3:46][C:43]([O:42][C:40]([N:30]([C:31]1[NH:32][C:33]([C:37]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]3[CH:18]=[C:17]([CH:19]4[CH2:20][CH2:21]4)[CH:16]=[C:13]([C:14]#[N:15])[CH:12]=3)[C:4]=2[F:22])=[O:38])=[C:34]([Cl:36])[N:35]=1)[C:28]([O:27][C:24]([CH3:23])([CH3:25])[CH3:26])=[O:29])=[O:41])([CH3:44])[CH3:45]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 68487554HCID 68487554, VerbindungHCID 178454348HCID 178454348, Verbindung

Produkt 1

HCID 178454346HCID 178454346, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-cyclopropylbenzonitrile (95 mg, 0.299 mmol), 2-(bis{[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-chloro-1H-imidazole-5-carboxylic acid (120 mg, 0.299 mmol) and HOBT (45.7 mg, 0.299 mmol) in DMF (3 ml) was added EDC (57.2 mg, 0.299 mmol) and the reaction mixture was stirred at RT for 45 minutes. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material bis(1,1-dimethylethyl)(4-chloro-5-{[({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-imidazol-2-yl)imidodicarbonate (165 mg, 0.250 mmol, 84% yield) was used directly in the next step. LC-MS (ES+) m/z 660 [M+H].

Aufarbeitung

  1. washwashed with water
  2. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-2679de7e8aa2410caa4a2f7f5f1b1be1
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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