1,2-Dichloroethane → HCID 178423795, Verbindung

HRID 888391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888391
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[C:11]([C:21](O)=[O:22])[CH:10]=1.Cl.Cl.[NH:26]1[CH:30]=[N:29][C:28]([C@H:31]([NH2:33])[CH3:32])=[N:27]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[CH:12]=[C:11]([C:21]([NH:33][C@@H:31]([C:28]2[N:29]=[CH:30][NH:26][N:27]=2)[CH3:32])=[O:22])[CH:10]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 687331912'-Fluoro-4'methyl-5-morpholin-4-ylbiphenyl-3-carboxylic acidHCID 178461973HCID 178461973, Verbindung

Produkt 1

HCID 178423795HCID 178423795, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2′-fluoro-4′methyl-5-morpholin-4-ylbiphenyl-3-carboxylic acid (52.0 mg, 0.15 mmol) in N,N-dimethylformamide (1.0 mL) was added (1R)-1-(1H-1,2,4-triazol-3-yl)ethanamine dihydrochloride (30.1 mg, 0.16 mmol), EDC (36.8 mg, 0.19 mmol), HOBT (22.6 mg, 0.15 mmol) and diisopropylethylamine (0.10 mL, 0.59 mmol). After 16 h, the mixture was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) to give the title compound. HRMS 410.1990 (M+1).). 1H NMR (500 MHz, CD3OD): δ 9.37 (s, 1H); 7.86 (d, J=7.6 Hz, 2H); 7.67 (s, 1H); 7.45 (t, J=8.1 Hz, 1H); 7.13 (d, J=7.9 Hz, 1H); 7.07 (d, J=12.0 Hz, 1H); 5.52-5.47 (m, 1H); 4.00 (t, J=4.6 Hz, 4H); 3.52 (t, J=4.5 Hz, 4H); 2.40 (s, 3H); 1.79 (d, J=7.1 Hz, 3H).

Aufarbeitung

  1. customthe mixture was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-1a60489b7e1a4988b3ef9e5fc92c306c
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247401B2

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