Triethylamine → n-Hydroxy-2-methyl-n'-pyridin-2-ylmethyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzamidine

HRID 471378ノート

反応式

HRID 471378 の反応式
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:26]([F:29])([F:28])[F:27])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)CCC1=O.[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH2:44][NH2:45].C(N(CC)CC)C>CN(C=O)C.C1COCC1>[OH:6][NH:5][C:4](=[N:45][CH2:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][N:38]=1)[C:3]1[CH:7]=[CH:8][C:9]([C:11]2[CH2:15][C:14]([C:26]([F:29])([F:27])[F:28])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)[O:13][N:12]=2)=[CH:10][C:2]=1[CH3:1]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 31398ChlorosuccinimideHCID 1371957342-Methyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime

生成物 1

HCID 136385979n-Hydroxy-2-methyl-n'-pyridin-2-ylmethyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzamidine収率 44%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

To a solution of 2-Methyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime (250 mg) in DMF (8 mL) was added N-chloro succinimide (84 mg) and heated to 75° C. for 1 h. After cooling, the reaction mixture was poured onto ice-water and extracted with EtOAc. The combined organic layers were washed with water, dried (Na2SO4) and concentrated in vacuoto ¼ of the original volume to obtain the crude hydroxamic acid chloride. This mixture was added to a solution of 2-picolylamine (65 mg) and triethylamine (0.15 mL, 0.11 g) in THF (8 mL) and stirred at room temperature over night. After concentration in vacuo, the mixture was purified by chromatography on silica gel to obtain the title compound (138 mg, 44%).

後処理

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto ice-water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuoto ¼ of the original volume
  7. customto obtain the crude hydroxamic acid chloride
  8. concentrationAfter concentration in vacuo
  9. customthe mixture was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-86f8b45c01bd4dc2af24519fcbd3d799
出典データセット
uspto-grants-2014_01
特許番号
US08633134B2

反応ノート

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