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Diisopropylethylamine → 2-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(trifluoromethyl)oxazole-4-carboxamide

HRID 881732
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HRID 881732 반응식
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.[CH3:17][C:18]1[O:19][C:20]([C:26]([F:29])([F:28])[F:27])=[C:21]([C:23](O)=[O:24])[N:22]=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.[Cl-].[Na+].O.O>[CH3:17][C:18]1[O:19][C:20]([C:26]([F:29])([F:27])[F:28])=[C:21]([C:23]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)=[O:24])[N:22]=1
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참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 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)

생성물 1

HCID 86700837
2-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(trifluoromethyl)oxazole-4-carboxamide
수율 47%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (420 mg, 1.917 mmol) in anhydrous DMF (9.6 mL) was added 2-methyl-5-(trifluoromethyl)oxazole-4-carboxylic acid (449 mg, 2.300 mmol) followed by DIPEA (1.0 mL, 5.75 mmol) and the mixture was stirred at room temperature for 10 minutes. HATU (875 mg, 2.300 mmol) was added and the mixture stirred at room temperature for 16 hours. The mixture was taken up in 1:1 mixture of brine and water and extracted with EtOAc. The organic portion was dried over sodium sulfate, filtered and concentrated to afford a brown oil, which was purified by flash column chromatography to afford the title compound as pale yellow solid after drying (360 mg, 47% yield). LC/MS, ESI-MS(+): 397.1, RT: 1.49 (Condition E).

후처리

  1. stirringthe mixture stirred at room temperature for 16 hours
  2. extractionextracted with EtOAc
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a brown oil, which
  7. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-acddda486ab8432eba5665004956429a
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08993619B2

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