Oxalyl chloride → 2-[1-Ethyl-3-trifluoromethylpyrazol-5-yl carbamoyl]-3-methyl-N-(1-methylethyl)benzamide

HRID 352448ノート

反応式

HRID 352448 の反応式
[CH2:1]([N:3]1[C:7](C(O)=O)=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[N:4]1)[CH3:2].[C:15](Cl)(=[O:19])C(Cl)=O.N[C:22]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:23]=1[C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:25].C([N:38](CC)C(C)C)(C)C>C(Cl)Cl.CN(C)C=O>[CH2:1]([N:3]1[C:7]([NH:38][C:15]([C:22]2[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:23]=2[C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:25])=[O:19])=[CH:6][C:5]([C:11]([F:12])([F:13])[F:14])=[N:4]1)[CH3:2]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 70177771-Ethyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidHCID 167760932-amino-3-methyl-N-(1-methylethyl)benzamide

生成物 1

HCID 227120622-[1-Ethyl-3-trifluoromethylpyrazol-5-yl carbamoyl]-3-methyl-N-(1-methylethyl)benzamide収率 54.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-ethyl-3-trifluoromethyl-pyrazol-5-yl carboxylic acid (0.5 g, 2.4 mmol) stirring in 20 mL of methylene chloride, oxalyl chloride (1.2 mL, 14 mmol) was added. Upon addition of 2 drops of N,N-dimethylformamide, foaming and bubbling occurred. The reaction mixture was heated at reflux for 1 hr as a yellow solution. After cooling, the solvent was removed in vacuo and the resulting residue dissolved in 20 mL of tetrahydrofuran. To the stirred solution, 2-amino-3-methyl-N-(1-methylethyl)benzamide (0.7 g, 3.6 mmol) was added followed by the dropwise addition of N,N-diisopropylethylamine (3 mL, 17 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between ethyl acetate (100 mL) and 1N aqueous hydrochloric acid (75 mL). The separated organic layer was washed with water and brine and dried over magnesium sulfate. Evaporating in vacuo gave a white solid residue, which on purification by flash column chromatography on silica gel (2:1 hexanes/ethyl acetate) afforded 0.5 g of the title compound, a compound of the present invention, melting at 223-226° C.

後処理

  1. custombubbling
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1 hr as a yellow solution
  4. temperatureAfter cooling
  5. customthe solvent was removed in vacuo
  6. dissolutionthe resulting residue dissolved in 20 mL of tetrahydrofuran
  7. customthe reaction mixture was partitioned between ethyl acetate (100 mL) and 1N aqueous hydrochloric acid (75 mL)
  8. washThe separated organic layer was washed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. customEvaporating in vacuo
  11. customgave a white solid residue, which
  12. customon purification by flash column chromatography on silica gel (2:1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-68467c6a4a1b4dd6be34fc536b7d1c57
出典データセット
uspto-grants-2004_06
特許番号
US06747047B2

反応ノート

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