Triethylamine → N-cyclopropyl-3-(difluoromethyl)-1-methyl-N-{1-[methyl(phenyl)-amino]propan-2-yl}-1H-pyrazole-4-carboxamide

HRID 77695노트

반응식

HRID 77695 반응식
[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[CH:13]1([NH:16][CH:17]([CH3:27])[CH2:18][N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.C(N(CC)CC)C.CCCCCCC.C(OCC)(=O)C>O1CCCC1>[CH:13]1([N:16]([CH:17]([CH3:27])[CH2:18][N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([C:7]2[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=2)=[O:9])[CH2:15][CH2:14]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 21899848Ethylacetate heptaneHCID 68557675N2-cyclopropyl-N1-methyl-N1-phenylpropane-1,2-diamine

생성물 1

HCID 67071695N-cyclopropyl-3-(difluoromethyl)-1-methyl-N-{1-[methyl(phenyl)-amino]propan-2-yl}-1H-pyrazole-4-carboxamide수율 40.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

At ambient temperature, a solution of 220 mg (1.13 mmol) of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride in 1 ml of tetrahydrofurane is added dropwise to a solution of 210 mg (1.03 mmol) of N2-cyclopropyl-N1-methyl-N1-phenylpropane-1,2-diamine and 0.16 ml (1.13 mmol) of triethylamine in 5 ml of tetrahydrofurane. The reaction mixture is stirred for 15 hrs at room temperature. The solvent to is removed under vacuum and 100 ml of water are then added to the residue. The watery layer is extracted twice with ethyl acetate (2×150 ml) and the combined organic layers are successively washed by a 1 N solution of HCl, a saturated solution of potassium carbonate and brine and filtered over a ChemElut cartridge to yield after concentration 180 mg of a brown oil. Column chromatography (gradient heptane/ethyl acetate) yielded 150 mg (38% yield) of N-cyclopropyl-3-(difluoromethyl)-1-methyl-N-{1-[methyl(phenyl)-amino]propan-2-yl}-1H-pyrazole-4-carboxamide as a yellow oil (M+H=363).

후처리

  1. customThe solvent to is removed under vacuum and 100 ml of water
  2. additionare then added to the residue
  3. extractionThe watery layer is extracted twice with ethyl acetate (2×150 ml)
  4. washthe combined organic layers are successively washed by a 1 N solution of HCl
  5. filtrationa saturated solution of potassium carbonate and brine and filtered over a ChemElut cartridge
  6. customto yield after concentration 180 mg of a brown oil

출처 및 근거

ORD 기록
ord-190cce6815b146d6958063d1e972cc95
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841332B2

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