Diisopropylethylamine → HCID 86711436, compound

HRID 1401093Notes

Reaction equation

HRID 1401093 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]([CH3:19])[CH3:18])[CH:15]=2)[C:10]([CH:20]=[CH:21][C:22](O)=[O:23])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=1)[C:29]([NH:31][NH:32][CH:33]([CH3:35])[CH3:34])=[O:30].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:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=1)[C:29]([NH:31][N:32]([C:22](=[O:23])/[CH:21]=[CH:20]/[C:10]1[C:11]2[C:16](=[CH:15][C:14]([CH:17]([CH3:18])[CH3:19])=[CH:13][CH:12]=2)[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH:9]=1)[CH:33]([CH3:35])[CH3:34])=[O:30]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86711429HCID 86711429, compoundHCID 86711437HCID 86711437, compound

Product 1

HCID 86711436HCID 86711436, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution containing 3-(1-(tert-butoxycarbonyl)-6-isopropyl-1H-indol-3-yl)acrylic acid (183.0 mg, 0.56 mmol), 3-fluoro-N′-isopropylbenzohydrazide (163.5 mg, 0.83 mmol) and HATU (316.9 mg, 0.83 mmol) dissolved in DMF (3.0 ml), N,N-diisopropylethylamine (DIPEA)(0.14 ml, 0.83 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 (33% EtOAc) for refinement, and dried so that white (E)-tert-butyl 3-(3-(2-(3-fluorobenzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-5-methyl-1H-indole-1-carboxylate was obtained (138.0 mg, 48.6%).

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 (33% EtOAc) for refinement
  6. dry with materialdried so that white (E)-tert-butyl 3-(3-(2-(3-fluorobenzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-5-methyl-1H-indole-1-carboxylate
  7. customwas obtained (138.0 mg, 48.6%)

Sources & evidence

ORD record
ord-aaa016416fc4404bba223432a4e1c8f0
Source dataset
uspto-grants-2014_12
Patent number
US08906952B2

Reaction notes

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