Ammonium Chloride → 5-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxamide

HRID 733128ノート

反応式

HRID 733128 の反応式
[C:1]([C:5]1[N:9]([C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH:13]=[CH:14][CH:15]=2)[N:8]=[C:7]([C:23]([OH:25])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:32]C=2C=1.C(N(CC)C(C)C)C.[Cl-].[NH4+]>CN(C=O)C>[C:1]([C:5]1[N:9]([C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH:13]=[CH:14][CH:15]=2)[N:8]=[C:7]([C:23]([NH2:32])=[O:25])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 521913N,N-Diethyl-2-propanamineHCID 112796905-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxylic acid

生成物 1

HCID 113826455-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxamide収率 103.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the carboxylic acid (0.062 g, 0.17 mmol) in DMF (1 ml) were added pyBOP (0.138 g, 0.26 mmol), HOBT (0.035 g, 0.2 mmol), diethylisopropylamine (0.147 ml, 0.87 mmol) and ammonium chloride (0.056 g, 1.05 mmol). The reaction mixture was stirred at room temperature for 16 hours, then cooled and partitioned between ethylacetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification of the crude product by silica-gel chromatography (3:2 hexanes/ethylacetate) yielded the product (0.062 g, 64%) as a solid.

後処理

  1. temperaturecooled
  2. custompartitioned between ethylacetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude product by silica-gel chromatography (3:2 hexanes/ethylacetate)

出典と根拠

ORDレコード
ord-be7ac90ca35c4ec0ad5442cbff5b3004
出典データセット
uspto-grants-2009_09
特許番号
US07589116B2

反応ノート

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