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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
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HRID 1478179 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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-one2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-cc2f8a77f01b41deb666542b386424d8
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09403810B2

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