Diisopropylethylamine → benzyl 2-(5-(4'-(2-methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetate

HRID 515391노트

반응식

HRID 515391 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:19][O:18][CH:17]([CH2:20][C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:22])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:31][C:32]1[O:33][C:34]([C:40]([F:43])([F:42])[F:41])=[C:35]([C:37](O)=[O:38])[N:36]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:31][C:32]1[O:33][C:34]([C:40]([F:43])([F:41])[F:42])=[C:35]([C:37]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[CH:10][C:11]([CH:14]4[CH2:19][O:18][CH:17]([CH2:20][C:21]([O:23][CH2:24][C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)=[O:22])[CH2:16][CH2:15]4)=[CH:12][CH:13]=3)=[CH:4][CH:3]=2)=[O:38])[N:36]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27756512-methyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89872737benzyl 2-(5-(4'-amino-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetate

생성물 1

HCID 89872728benzyl 2-(5-(4'-(2-methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetate수율 81.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of benzyl 2-(5-(4′-amino-[1,1′-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetate (118 mg, 0.294 mmol) in DMF (2 ml) at room temperature was added 2-methyl-5-(trifluoromethyl)oxazole-4-carboxylic acid (74.5 mg, 0.382 mmol) and DIPEA (0.103 ml, 0.588 mmol) and the reaction was stirred at room temperature for 10 min then was added HATU (145 mg, 0.382 mmol). The reaction was stirred at room temperature for 30 min. The reaction was quenched by brine and was extracted with EtOAc. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (10 to 50% EtOAc/Heptane) to give the title compound 138 mg (yield 81%). MS (ESI) m/z 579.4 (M+1). Retention time 1.69 min (condition A).

후처리

  1. stirringThe reaction was stirred at room temperature for 30 min
  2. customThe reaction was quenched by brine
  3. extractionwas extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (10 to 50% EtOAc/Heptane)

출처 및 근거

ORD 기록
ord-812cb9a344b54bafa33bb1a21351a731
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108956B2

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