HCID 24954329、化合物 → 4-Methyl-2-{6-[2-(4-trifluoromethyl-phenyl)-ethyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamide

HRID 1879147ノート

反応式

HRID 1879147 の反応式
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](/[CH:22]=[CH:23]/[C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[N:17]=2)=[N:13][C:12]=1[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.C(O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18]([CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:28][CH:29]=3)[N:17]=2)=[N:13][C:12]=1[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 1

HCID 24954329HCID 24954329、化合物

生成物 1

HCID 249547004-Methyl-2-{6-[2-(4-trifluoromethyl-phenyl)-ethyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamide収率 51.8%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 21584252Ethanol ethylacetate溶媒

実験手順

To a solution of 4-methyl-2-{6-[(E)-2-(4-trifluoromethyl-phenyl)-vinyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamide (40 mg, 0.08 mmol, 1.0 equiv) in ethyl acetate/ethanol (1:1) was added Pd(OH)2 (10 mg, 20%). The flask was first purged with nitrogen, then with hydrogen. The reaction mixture was stirred at ambient temperature for 3 hr and monitored by LCMS. Upon completion, the reaction mixture was diluted with ethyl acetate, filtered through Celite and concentrated in vacuo. The crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid) to afford 4-methyl-2-{6-[2-(4-trifluoromethyl-phenyl)-ethyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamide (20 mg, 50%). 1H NMR (400 MHz, CD2Cl2) δ 9.16 (s, 1H), 8.39 (s, 1H), 7.52 (d, J=8.0 Hz, 2H), 7.28-7.37 (m, 7H), 6.25 (bs, 1H), 4.60 (d, J=8.0 Hz, 2H), 3.19 (apparent s, 4H), 2.72 (s, 3H); HRMS (M+H)+=483.14.

後処理

  1. customThe flask was first purged with nitrogen
  2. additionUpon completion, the reaction mixture was diluted with ethyl acetate
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-d6eb9165629b498d98227f2d982a37b6
出典データセット
uspto-grants-2012_11
特許番号
US08314138B2

反応ノート

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