1-Isocyanato-2-phenoxybenzene → 5-(2-hydroxyphenyl)-N-(2-phenoxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 1712958노트

반응식

HRID 1712958 반응식
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:2]=[O:3].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH2:27][CH:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[OH:34])[NH:25][N:24]=2)[CH:18]=1>CN(C=O)C.ClCCCl.C(=O)(O)[O-].[Na+]>[OH:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH:26]1[N:25]([C:2]([NH:1][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:3])[N:24]=[C:23]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[CH2:27]1

참가 물질

6

반응물 2

HCID 27333891-Isocyanato-2-phenoxybenzeneHCID 226963962-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol

생성물 1

HCID 249643015-(2-hydroxyphenyl)-N-(2-phenoxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide수율 12.9%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 1-isocyanato-2-phenoxybenzene (29.14 mg, 0.138 mmol) in DMF (0.5 mL) was added a solution of 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (29.9 mg, 0.125 mmol) in DMF (0.5 mL) and DCE (0.5 mL) at rt. The reaction mixture was shaken at rt for 20 h. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (2 mL) and extracted with DCM. The organic solutions were combined, dried over MgSO4, filtered, and concentrated. The residue was purified by RP-HPLC to give 5-(2-hydroxyphenyl)-N-(2-phenoxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (I-85) (7.24 mg, 12.8%). LCMS: (FA) ES+ 451.3.

후처리

  1. extractionextracted with DCM
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-ee5ea791f15e488aae2a131de2fff87c
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795249B2

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