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Dimethylformamide → 5-Bromo-N-(2-cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-4-methylisoxazole-3-carboxamide

HRID 1478179
ノート
印刷プレビュー

反応式

HRID 1478179 の反応式
CN(C=O)C.C(Cl)(=O)C(Cl)=O.[Br:12][C:13]1[O:17][N:16]=[C:15]([C:18]([OH:20])=O)[C:14]=1[CH3:21].[NH2:22][C:23]1[C:24](=[O:36])[N:25]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:26]([CH3:29])[C:27]=1[CH3:28].C(N(CC)CC)C>C(Cl)Cl>[Br:12][C:13]1[O:17][N:16]=[C:15]([C:18]([NH:22][C:23]2[C:24](=[O:36])[N:25]([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[N:26]([CH3:29])[C:27]=2[CH3:28])=[O:20])[C:14]=1[CH3:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 231371575-Bromo-4-methylisoxazole-3-carboxylic acidHCID 612730214-amino-2-cyclohexyl-1,5-dimethyl-2,3-dihydro-1H-pyrazol-3-one2 回

生成物 1

HCID 118511021
5-Bromo-N-(2-cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-4-methylisoxazole-3-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of DMF (5.33 mL, 68.8 mmol) in DCM (200 mL) was cooled to 0° C. and treated with oxalyl chloride (3.31 ml, 37.9 mmol). 5-bromo-4-methylisoxazole-3-carboxylic acid (7.09 g, 34.4 mmol) was added and stirred under ice cooling for 10 mins. 4-Amino-2-cyclohexyl-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate D) (7.92 g, 37.9 mmol) and triethylamine (14.39 ml, 103 mmol) were added at 0° C. and the mixture stirred at this temperature for 30 mins. The resulting mixture was diluted with DCM and washed with a saturated NaHCO3 (aq) solution. The organic layer was dried over MgSO4, filtered and the solvent removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 100% TBME afforded the title compound;

後処理

  1. stirringthe mixture stirred at this temperature for 30 mins
  2. washwashed with a saturated NaHCO3 (aq) solution
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe crude material was adsorbed onto silica and purification by chromatography
  7. washeluting with 100% TBME

出典と根拠

ORDレコード
ord-cc2f8a77f01b41deb666542b386424d8
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09403810B2

反応ノート

読み込み中…

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