Pyridine → 2-{[2-(4-Trifluoromethoxyphenoxy)-acetylamino]-methyl}thiazole-4-carboxylic acid [2-(3-chlorophenyl)-ethyl]amide

HRID 1009196ノート

反応式

HRID 1009196 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]=[C:15]([CH2:18][NH2:19])[S:16][CH:17]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1.[F:20][C:21]([F:35])([F:34])[O:22][C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29](Cl)=[O:30])=[CH:25][CH:24]=1.N1C=CC=CC=1.[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]=[C:15]([CH2:18][NH:19][C:29](=[O:30])[CH2:28][O:27][C:26]3[CH:32]=[CH:33][C:23]([O:22][C:21]([F:34])([F:20])[F:35])=[CH:24][CH:25]=3)[S:16][CH:17]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 27773084-(Trifluoromethoxy)phenoxyacetyl chlorideHCID 577870612-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide

生成物 1

HCID 116492242-{[2-(4-Trifluoromethoxyphenoxy)-acetylamino]-methyl}thiazole-4-carboxylic acid [2-(3-chlorophenyl)-ethyl]amide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide (0.54 g, 1.8 mmol) was dissolved in methylene chloride (15 mL). (4-Trifluoromethoxyphenoxy)-acetyl chloride (0.47 g, 1.8 mmol) was added followed by pyridine (0.3 mL, 4 mmol) and DMAP (0.02 g, 0.1 mmol). The mixture was stirred for 12 hours. Saturated, aqueous NH4Cl was added and the mixture was extracted with methylene chloride ×3. The combined organic extracts were washed with 1N HCl, saturated, aqueous NaHCO3, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The material was purified by recrystallization from ethanol/diethyl ether to afford the title compound (0.65 g, 68% from the Boc protected amine): 1H NMR (400 MHz, d6-DMSO): 9.08 (t, 1H), 8.40 (t, 1H), 8.10 (s, 1H), 7.27 (m, 5H), 7.17 (d, 1H), 7.06 (d, 2H), 4.65 (s, 2H), 4.62 (d, 2H), 3.48 (m, 2H), 2.84 (t, 2H); MS (ESI-LCMS) for C22H20ClF3N3O4S: 514 (MH+).

後処理

  1. extractionthe mixture was extracted with methylene chloride ×3
  2. washThe combined organic extracts were washed with 1N HCl
  3. dry with materialsaturated, aqueous NaHCO3, brine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe material was purified by recrystallization from ethanol/diethyl ether

出典と根拠

ORDレコード
ord-11890b3697214923a219aecc93b4e47c
出典データセット
uspto-grants-2011_07
特許番号
US07973061B2

反応ノート

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