1-Benzoyl-2-isopropylhydrazine → HCID 71468735, compound

HRID 1401086Notes

Reaction equation

HRID 1401086 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:5]2)[CH2:3][CH2:2]1.[CH:18]([NH:21][NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:20])[CH3:19].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>[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](/[CH:13]=[CH:14]/[C:15]([N:21]([CH:18]([CH3:20])[CH3:19])[NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:17])=[CH:5]2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 188691-Benzoyl-2-isopropylhydrazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86711431HCID 86711431, compound

Product 1

HCID 71468735HCID 71468735, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution containing (E)-3-(1-cyclopropyl-1H-indol-3-yl)acrylic acid (160 mg, 0.70 mmol, 1.0 equivalent), N′-isopropylbenzohydrazide (188.8 mg, 1.05 mmol, 1.5 equivalent) and HATU (401.5 mg, 1.05 mmol, 1.5 equivalent) dissolved in DMF (5.0 ml), N,N-diisopropylethylamine (DIPEA)(0.18 ml, 1.05 mmol, 1.5 equivalent) was slowly drop-wise added and stirred at room temperature for 24 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=1:1) and dried so that solid form of (E)-N′-(3-(1-cyclopropyl-1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide was obtained. (87.9 mg, 32%).

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=1:1)
  6. dry with materialdried so that solid form of (E)-N′-(3-(1-cyclopropyl-1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide
  7. customwas obtained

Sources & evidence

ORD record
ord-5b0822f7a0dc45b68d743474ae3c814f
Source dataset
uspto-grants-2014_12
Patent number
US08906952B2

Reaction notes

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