1-(4-fluorophenyl)-N-methylmethanamine → 2-{6-[(3-Methoxy-benzyl)-methyl-amino]-pyrazin-2-yl}-4-methyl-thiazole-5-carboxylic acid 4-fluoro-benzylamide

HRID 1879165

Reaktionsgleichung

Reaktionsgleichung von HRID 1879165
FC1C=CC(CNC)=CC=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[CH2:16][NH:17][CH3:18].[F:22][C:23]1[CH:45]=[CH:44][C:26]([CH2:27][NH:28][C:29]([C:31]2[S:35][C:34]([C:36]3[CH:41]=[N:40][CH:39]=[C:38](I)[N:37]=3)=[N:33][C:32]=2[CH3:43])=[O:30])=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:45]=[CH:44][C:26]([CH2:27][NH:28][C:29]([C:31]2[S:35][C:34]([C:36]3[CH:41]=[N:40][CH:39]=[C:38]([N:17]([CH2:16][C:15]4[CH:19]=[CH:20][CH:21]=[C:13]([O:12][CH3:11])[CH:14]=4)[CH3:18])[N:37]=3)=[N:33][C:32]=2[CH3:43])=[O:30])=[CH:25][CH:24]=1

Komponenten

4

Edukt 3

HCID 7368601-(4-fluorophenyl)-N-methylmethanamineHCID 51522253-Methoxy-N-methylbenzylamineHCID 866455582-(6-Iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro benzylamide

Produkt 1

HCID 249546992-{6-[(3-Methoxy-benzyl)-methyl-amino]-pyrazin-2-yl}-4-methyl-thiazole-5-carboxylic acid 4-fluoro-benzylamideAusbeute 75 %

Versuchsvorschrift

Following the procedure described in Example 14, making variations as required to replace 4-fluoro-N-methyl-benzylamine with (3-methoxy-benzyl)-methyl-amine to react with 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro benzylamide, the title compound was obtained in 75% yield. 1H NMR (400 MHz, CD2Cl2) δ 8.55 (s, 1H), 8.07 (s, 7.27-7.37 (M, 2H), 7.18-7.26 (m, 1H), 6.90-7.08 (m, 2H), 6.70-6.88 (m, 3H), 6.21 (bs, 1H), 4.79 (s, 2H), 4.53 (d, J=4.0 Hz, 2H), 3.72 (s, 3H), 3.15 (s, 3H), 2.69 (s, 3H); MS (ES+) m/z 478.2 (M+1), Rt=1.58 min.

Quellen und Nachweise

ORD-Eintrag
ord-e8ab899f041c4e688cd0e93f3a96650c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314138B2

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