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

HRID 471370ノート

反応式

HRID 471370 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([CH:18]=[N:19][OH:20])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClN1C(=O)CCC1=O.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42][NH2:43].C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:19][OH:20])=[N:43][CH2:42][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=4)=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 25517Ammonium ChlorideHCID 31398ChlorosuccinimideHCID 1363862674-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde oxime

生成物 1

HCID 1363411544-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-hydroxy-2-methyl-N'-pyridin-2-ylmethyl-benzamidine収率 42%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde-oxime ((i.e. the product of Example 1 Step 2, 177 mg, 0.42 mmol) in DMF (4 mL) was added N-chlorosuccinimide (67 mg, 0.50 mmol) and the mixture was stirred at 70° C. bath temperature for 30 min. After cooling to 0° C., picolylamine (85 mg, 0.79 mmol) and triethylamine (145 mg, 1.44 mmol) was added. The mixture was allowed to war to room temperature over night and was then poured on ice water. The pH was adjusted to 7 by addition of NH4Cl and the resulting precipitate was filtered off. The crude product was then purified by column chromatography on SiO2 (CH2Cl2: MeOH=96:4) to give the title compound (75 mg, 42%).

後処理

  1. temperatureAfter cooling to 0° C.
  2. waitThe mixture was allowed to war to room temperature over night
  3. additionwas then poured on ice water
  4. filtrationthe resulting precipitate was filtered off
  5. customThe crude product was then purified by column chromatography on SiO2 (CH2Cl2: MeOH=96:4)

出典と根拠

ORDレコード
ord-973c6622ab56469b991bcd590b10abed
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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