Diisopropylethylamine → HCID 118071489, compound

HRID 2207746Notes

Reaction equation

HRID 2207746 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[C:16]([NH:18][CH3:19])=[O:17].[F:20][CH:21]([CH3:25])[C:22](O)=[O:23].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(#N)C>[F:20][CH:21]([CH3:25])[C:22]([NH:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[C:16]([NH:18][CH3:19])=[O:17])=[O:23]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2568762-Fluoropropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118071469HCID 118071469, compound

Product 1

HCID 118071489HCID 118071489, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(2-aminoethyl)-5-methoxy-N-methyl-1H-indole-2-carboxamide hydrochloride (90.0 mg) and acetonitrile (5.00 mL) were added 2-fluoropropionic acid (0.0495 mL), diisopropylethylamine (0.272 mL), and 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (181 mg), followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:0 to 10:1). The obtained residue was solidified with a mixed solvent of hexane:ethyl acetate=2:1 to obtain 3-{2-[(2-fluoropropanoyl)amino]ethyl}-5-methoxy-N-methyl-1H-indole-2-carboxamide (70.0 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:0 to 10:1)

Sources & evidence

ORD record
ord-730136be1f634895802f083ae0d3e01a
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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