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Water → 2-{2-[1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-3-phenyl-N-(tetrahydro-2H-pyran-4-ylmethyl)propanamide

HRID 1750433
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HRID 1750433 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]([CH:22]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:23]([OH:25])=O)[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.[O:57]1[CH2:62][CH2:61][CH:60]([CH2:63][NH2:64])[CH2:59][CH2:58]1.O>CN(C=O)C>[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]([CH:22]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:23]([NH:64][CH2:63][CH:60]3[CH2:61][CH2:62][O:57][CH2:58][CH2:59]3)=[O:25])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 27732104-AminomethyltetrahydropyranHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867212752-(2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)-3-phenylpropanoic acid

생성물 1

HCID 86721276
2-{2-[1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-3-phenyl-N-(tetrahydro-2H-pyran-4-ylmethyl)propanamide
수율 17.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of the compound (11 mg, 0.02 mmol) obtained in step 2, HATU (76 mg, 0.20 mmol), DEIA (5.13 μL, 0.03 mmol) and (tetrahydro-2H-pyran-4-yl)methanamine (3.04 μL, 0.03 mmol) in DMF (2 mL) was stirred at room temperature for 1 day. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed to with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane) to give the title compound (1.9 mg, 3.48 μmol, 14.2%) as a white powder.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed to with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-1929ea3abe294b778e3d7d02bf00a84e
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156837B2

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