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

HRID 881734
Notes
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Reaction equation

HRID 881734 reaction equation
[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.[CH2:17]([C:19]1[O:20][C:21]([C:25](O)=[O:26])=[C:22]([CH3:24])[N:23]=1)[CH3:18].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>[CH2:17]([C:19]1[O:20][C:21]([C:25]([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:26])=[C:22]([CH3:24])[N:23]=1)[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 138352982-Ethyl-4-methyl-1,3-oxazole-5-carboxylic acid

Product 1

HCID 86700839
2-ethyl-4-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazole-5-carboxamide
Yield 52.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (360 mg, 1.643 mmol) in anhydrous DMF (8.2 mL) was added 2-ethyl-4-methyloxazole-5-carboxylic acid (306 mg, 1.972 mmol), followed by DIPEA (0.86 mL, 4.93 mmol) and the mixture was stirred at room temperature for 10 minutes. HATU (750 mg, 1.972 mmol) was added and the mixture was stirred at room temperature for 16 hour. The mixture was taken up in 1:1 mixture of brine and water (40 mL) and extracted with EtOAc (60 mL). 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 (305 mg, 52% yield) as a white solid. LC/MS, ESI-MS (+): 357.1, RT: 1.35 (Condition E).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hour
  2. extractionextracted with EtOAc (60 mL)
  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

Sources & evidence

ORD record
ord-176d063d63844eac8fbeb4ca21546df7
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993619B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes