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p-Fluorobenzoic acid 2-isopropylhydrazide → HCID 86711457, compound

HRID 1401106
Notes
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Reaction equation

HRID 1401106 reaction equation
[CH3:1][C:2]([CH3:19])=[CH:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:6]1.[F:20][C:21]1[CH:33]=[CH:32][C:24]([C:25]([NH:27][NH:28][CH:29]([CH3:31])[CH3:30])=[O:26])=[CH:23][CH:22]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[F:20][C:21]1[CH:33]=[CH:32][C:24]([C:25]([NH:27][N:28]([CH:29]([CH3:30])[CH3:31])[C:16](=[O:18])/[CH:15]=[CH:14]/[C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]([CH2:4][CH:3]=[C:2]([CH3:1])[CH3:19])[CH:6]=2)=[O:26])=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 18030p-Fluorobenzoic acid 2-isopropylhydrazideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86711430HCID 86711430, compound

Product 1

HCID 86711457HCID 86711457, compound

Reagents, catalysts & solvents

2
HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution containing (E)-3-(1-(3-methylbut-2-enyl)-1H-indol-3-yl)acrylic acid (161 mg, 0.63 mmol), 4-fluoro-N′-isopropylbenzohydrazide (82.4 mg, 0.42 mmol) and HATU (239.5 mg, 0.63 mmol) dissolved in DMF (3.0 ml), N,N-diisopropylethylamine (DIPEA)(0.11 ml, 0.63 mmol) was slowly drop-wise added and stirred at room temperature for 12 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (35% EtOAc) for refinement and dried so that ivory (E)-4-fluoro-N′-isopropyl-N′-(3-(1-(3-methylbut-2-enyl)-1H-indol-3-yl)acryloyl)benzohydrazide was obtained (116.0 mg, 42.5%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated through silica gel chromatography (35% EtOAc) for refinement
  6. dry with materialdried so that ivory (E)-4-fluoro-N′-isopropyl-N′-(3-(1-(3-methylbut-2-enyl)-1H-indol-3-yl)acryloyl)benzohydrazide
  7. customwas obtained (116.0 mg, 42.5%)

Sources & evidence

ORD record
ord-c4addd7e43754c118f376c1ea92fa4ec
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906952B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes