Diisopropylethylamine → 1-({2-[1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}acetyl)piperidin-4-one

HRID 1750345노트

반응식

HRID 1750345 반응식
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23](O)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O.Cl.[NH:61]1[CH2:66][CH2:65][C:64](=[O:67])[CH2:63][CH2:62]1>CN(C=O)C.O>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([N:61]3[CH2:66][CH2:65][C:64](=[O:67])[CH2:63][CH2:62]3)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:3])([CH3:2])[CH3:4]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2723901PiperonylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867211822-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid

생성물 1

HCID 867211831-({2-[1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}acetyl)piperidin-4-one수율 60%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of the compound (60 mg, 0.17 mmol) obtained in step 6, HATU (76 mg, 0.20 mmol), DIEA (0.035 mL, 0.20 mmol) and piperidin-4-one monohydrochloride monohydrate (30.8 mg, 0.20 mmol) in DMF (1.5 mL) was stirred at room temperature for 4 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→100% ethyl acetate/hexane) to give the title compound (44 mg, 0.100 mmol, 60%) as a white powder.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→100% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-2fdb94dfbcd84cf2a725b7855591916e
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156837B2

반응 노트

불러오는 중…