Trifluoroacetic acid → N-{4-[4-[(4-chlorophenyl)(hydroxy)methyl]-5-(1H-imidazol-2-yl)-1,3-thiazol-2-yl]pyridin-2-yl}acetamide

HRID 2401795ノート

反応式

HRID 2401795 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:37])[C:9]2[N:10]=[C:11]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH:33][C:34](=[O:36])[CH3:35])[CH:28]=3)[S:12][C:13]=2[C:14]2[N:15](COCC[Si](C)(C)C)[CH:16]=[CH:17][N:18]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:37])[C:9]2[N:10]=[C:11]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH:33][C:34](=[O:36])[CH3:35])[CH:28]=3)[S:12][C:13]=2[C:14]2[NH:18][CH:17]=[CH:16][N:15]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 66749292N-{4-[4-[(4-chlorophenyl)(hydroxy)methyl]-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-1,3-thiazol-2-yl]pyridin-2-yl}acetamide

生成物 1

HCID 66749295N-{4-[4-[(4-chlorophenyl)(hydroxy)methyl]-5-(1H-imidazol-2-yl)-1,3-thiazol-2-yl]pyridin-2-yl}acetamide収率 54.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-{4-[4-[(4-chlorophenyl)(hydroxy)methyl]-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-1,3-thiazol-2-yl]pyridin-2-yl}acetamide (0.120 g, 0.216 mmol) was dissolved in DCM (5 mL) and trifluoroacetic acid (5.0 mL, 65 mmol) was added. The mixture was stirred at room temperature overnight. The solvent was evaporated, azeotroped with toluene and purified using column chromatography on silica gel (0 to 10% MeOH in DCM) to give the title compound (0.050 g, 50%). LCMS: (FA) ES+, 426, 428. 1H NMR (400 MHz, d4-methanol) δ: 8.68 (s, 1H), 8.38 (d, J=5.24 Hz, 1H), 7.64 (dd, J=5.25, 1.60 Hz, 1H), 7.45-7.37 (m, 2H), 7.30-7.23 (m, 2H), 7.25-7.09 (m, 2H), 6.37 (s, 1H), 2.20 (s, 3H).

後処理

  1. customThe solvent was evaporated
  2. customazeotroped with toluene
  3. custompurified

出典と根拠

ORDレコード
ord-1cfadb53931e43808797954fba17ccdc
出典データセット
uspto-grants-2014_08
特許番号
US08796268B2

反応ノート

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