Sulfuric Acid → 3-(3,5-difluorophenyl)-5-methyl-N-(1H-pyrazol-4-ylmethyl)-4,5-dihydro-1,2-oxazole-5-carboxamide

HRID 1522765노트

반응식

HRID 1522765 반응식
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][NH2:8])[CH:4]=[N:3]1.C(N(CC)C(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[F:39][C:40]1[CH:41]=[C:42]([C:47]2[CH2:51][C:50]([CH3:55])([C:52](O)=[O:53])[O:49][N:48]=2)[CH:43]=[C:44]([F:46])[CH:45]=1.OS(O)(=O)=O>ClCCl>[F:46][C:44]1[CH:43]=[C:42]([C:47]2[CH2:51][C:50]([CH3:55])([C:52]([NH:8][CH2:7][C:5]3[CH:6]=[N:2][NH:3][CH:4]=3)=[O:53])[O:49][N:48]=2)[CH:41]=[C:40]([F:39])[CH:45]=1

참가 물질

8

반응물 6

HCID 1118Sulfuric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57415873(1H-Pyrazol-4-yl)methanamine hydrochlorideHCID 683869243-(3,5-Difluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid

생성물 1

HCID 683867093-(3,5-difluorophenyl)-5-methyl-N-(1H-pyrazol-4-ylmethyl)-4,5-dihydro-1,2-oxazole-5-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1-(1H-Pyrazol-4-yl)methanamine hydrochloride (609 mg, 4.56 mmol), N,N-diisopropylethylamine (1.61 g, 12.44 mmol), HOBt (506 mg, 4.15 mmol) and EDCI (1.59 g, 8.29 mmol) were added to a solution of 3-(3,5-difluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid (1.00 g, 4.15 mmol) in dichloromethane (30 ml), and the mixture was stirred at RT for 16 h. H2SO4 (0.5M, 10 ml) was then added, and the mixture was diluted with CH2Cl2 (20 ml). The aqueous phase was extracted with CH2Cl2 (2×20 ml), the combined organic phases were washed with saturated NaHCO3 solution (30 ml) and dried over Na2SO4, and the solvent was removed. This gave 1.2 g of 3-(3,5-difluorophenyl)-5-methyl-N-(1H-pyrazol-4-ylmethyl)-4,5-dihydro-1,2-oxazole-5-carboxamide which was used without further purification.

후처리

  1. extractionThe aqueous phase was extracted with CH2Cl2 (2×20 ml)
  2. washthe combined organic phases were washed with saturated NaHCO3 solution (30 ml)
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed
  5. customThis gave 1.2 g of 3-(3,5-difluorophenyl)-5-methyl-N-(1H-pyrazol-4-ylmethyl)-4,5-dihydro-1,2-oxazole-5-carboxamide which was used without further purification

출처 및 근거

ORD 기록
ord-3c291fd07bd9452cb2ceca067255dbbc
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09078442B2

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