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

HRID 733128노트

반응식

HRID 733128 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-be7ac90ca35c4ec0ad5442cbff5b3004
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589116B2

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