Diisopropylethylamine → HCID 178432872, Verbindung

HRID 1875212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875212
[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[F:19])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:21][C:22]1[N:23]=[C:24]([CH3:30])[NH:25][C:26]=1[C:27](O)=[O:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:21][C:22]1[N:23]=[C:24]([CH3:30])[NH:25][C:26]=1[C:27]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[F:19])[C:4]=1[F:20])=[O:28]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68722395HCID 68722395, VerbindungHCID 178432882HCID 178432882, Verbindung

Produkt 1

HCID 178432872HCID 178432872, VerbindungAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile (40.0 mg, 0.136 mmol), 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (21.79 mg, 0.136 mmol) and HATU (51.6 mg, 0.136 mmol) in DMF (3 ml) was added diisopropylethyl amine (0.047 ml, 0.271 mmol) and the reaction mixture was stirred at rt for 15 minutes. The reaction mixture was purified via reverse phase HPLC and neutralized to give 4-chloro-N-({4-chloro-3-[(4-cyano-2-fluorophenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide (13 mg, 0.030 mmol, 22% yield) 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.73 (d, 1H), 7.47 (d, 1H), 7.29-7.42 (m, 2H), 6.87 (t, 1H), 4.52-4.73 (m, 2H), 2.34 (s, 3H). LC-MS (ES+) m/z 437.11, [M+H].

Aufarbeitung

  1. customThe reaction mixture was purified via reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b0a556e72ebb4a268b7697ccf50117ff
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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