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4-(Trifluoromethoxy)benzylamine → 2-[(4-Trifluoromethoxy-benzylamino)-methyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide hydrochloride

HRID 1009203
ノート
印刷プレビュー

反応式

HRID 1009203 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]([CH2:19][NH2:20])[S:17][CH:18]=2)=[O:13])[CH:6]=[CH:7][CH:8]=1.[F:21][C:22]([F:33])([F:32])[O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]N)=[CH:26][CH:25]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.C(O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]([CH2:19][NH:20][CH2:28][C:27]3[CH:30]=[CH:31][C:24]([O:23][C:22]([F:21])([F:32])[F:33])=[CH:25][CH:26]=3)[S:17][CH:18]=2)=[O:13])[CH:6]=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 5718464-(Trifluoromethoxy)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 673043282-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide hydrochloride

生成物 1

HCID 673043512-[(4-Trifluoromethoxy-benzylamino)-methyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide hydrochloride

試薬・触媒・溶媒 2

HCID 176
Acetic Acid
触媒
HCID 702Ethanol溶媒

実験手順

2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide hydrochloride (0.10 g, 0.3 mmol) and 4-(trifluoromethoxy)benzyl amine (0.06 g, 0.3 mmol) were mixed with sodium cyanoborohydride (1 M in THF, 0.6 mL), ethanol (5 mL), and a catalytic amount of acetic acid (2 drops). The mixture was heated at reflux for 24 hours. The mixture was concentrated in vacuo, diluted with water and extracted with methylene chloride. The combined organic layers were washed with sodium carbonate and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude amine was purified by flash chromatography (EtOAc/hexane), treated with HCl in dioxane, and concentrated in vacuo to afford the title compound: 1H NMR (400 MHz, d6-DMSO): 9.83 (br s, 2H), 8.43 (t, 1H), 8.32 (s, 1H), 7.66 (d, 2H), 7.44 (d, 2H), 7.25 (m, 4H), 4.58 (s, 2H), 4.37 (s, 2H), 3.53 (m, 2H), 2.86 (t, 2H); MS (ESI-LCMS) for C21H20ClF3N3O2S: 470 (MH+).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with methylene chloride
  6. washThe combined organic layers were washed with sodium carbonate and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude amine was purified by flash chromatography (EtOAc/hexane)
  11. additiontreated with HCl in dioxane
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e0fed782977a4e8181fa16522db0bb7c
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07973061B2

反応ノート

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