1-Hydroxybenzotriazole → 2-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide

HRID 877031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877031
[CH3:1][N:2]1[C:7]2=[CH:8][S:9][C:10](C)=[C:6]2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[F:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[C:26]1[N:27]=[C:28]([NH2:31])[S:29][CH:30]=1.CCN=C=NC[CH2:38][CH2:39]N(C)C.Cl.C1C=CC2N([OH:53])N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[CH3:1][N:2]1[C:10]2[S:9][CH:8]=[C:7]([CH2:38][C:39]([NH:31][C:28]3[S:29][CH:30]=[C:26]([C:17]4[CH:18]=[CH:19][C:20]([C:22]([F:23])([F:25])[F:24])=[CH:21][C:16]=4[F:15])[N:27]=3)=[O:53])[C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 404805694-(2-Fluoro-4-(trifluoromethyl)phenyl)thiazol-2-amineHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 469278392-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (150 mg, 0.590 mmol) with 4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (155 mg, 0.590 mmol) in the presence of EDCI hydrochloride (135 mg, 0.708 mmol), HOBt (24 mg, 0.177 mmol) and DMAP (7.21 mg, 0.059 mmol) in 1,2 dichloroethane (6 ml) to give 35 mg of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.19 (s, 3H), 3.47 (s, 3H), 4.08 (s, 2H), 7.08 (s, 1H), 7.70-7.84 (m, 3H), 8.23-8.28 (m, 1H), 12.52 (br s, 1H); APCI-MS (m/z) 497.21 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-e6ba10fdf76c41a2bd1cc231fd88d393
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987278B2

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