1-Benzoyl-2-isopropylhydrazine → HCID 71468594, compound

HRID 1401080Notes

Reaction equation

HRID 1401080 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([OH:14])=O)=[CH:2]1.[CH:15]([NH:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:17])[CH3:16].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>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([N:18]([CH:15]([CH3:17])[CH3:16])[NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:14])=[CH:2]1

Participants

7

Reactant 4

HCID 188691-Benzoyl-2-isopropylhydrazineHCID 81531DiisopropylethylamineHCID 53750483-Indoleacrylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71468594HCID 71468594, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution containing (E)-3-(1H-indol-3-yl)acrylic acid (200 mg, 1.06 mmol), N′-isopropylbenzohydrazide (283.4 mg, 1.59 mmol) and HATU (604.6 mg, 1.59 mmol) dissolved in DMF (7.0 ml), N,N-diisopropylethylamine (DIPEA)(0.277 ml, 1.59 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 (n-hexane:EtOAc:methanol=15:3:1) and dried so that white solid form of (E)-N′-(3-(1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide was obtained (327 mg, 88%).

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 (n-hexane:EtOAc:methanol=15:3:1)
  6. dry with materialdried so that white solid form of (E)-N′-(3-(1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide
  7. customwas obtained (327 mg, 88%)

Sources & evidence

ORD record
ord-2d5f68f2ddfb49aa8e743967ed6963a6
Source dataset
uspto-grants-2014_12
Patent number
US08906952B2

Reaction notes

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