Diisopropylethylamine → HCID 67973932, compound

HRID 1777699Notes

Reaction equation

HRID 1777699 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:18])[C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][NH2:32].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>[Cl:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][NH:32][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH3:18])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 61984652HCID 61984652, compound

Product 1

HCID 67973932HCID 67973932, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-((3-fluorophenyl)(methyl)amino)benzoic acid (0.100 g, 0.407 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.094 g; 0.407 mmol), HATU (0.170 g; 0.448 mmol) and N,N-diisopropylethylamine (0.176 mL; 1.02 mmol) in DMF (5 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in dichloromethane) to yield 0.048 g (28%) of the title compound as a white solid.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-41828336ae25481998f36ae0123609f0
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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