Diisopropylethylamine → HCID 72710870, compound

HRID 2207744Notes

Reaction equation

HRID 2207744 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C:8]=1[C:18]([OH:20])=O)(=[O:3])[CH3:2].[CH:21]([N:24](C(C)C)CC)(C)C.Cl.CN.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C:8]=1[C:18]([NH:24][CH3:21])=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 608124HCID 608124, compoundHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 72710870HCID 72710870, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(2-acetamidoethyl)-5-methoxy-1H-indole-2-carboxylic acid (100 mg), diisopropylethylamine (0.310 mL), methylamine hydrochloride (73.3 mg), and N,N-dimethyl formamide (1.75 mL) was added 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (206 mg), followed by stirring at room temperature overnight. To the mixture was added ice water, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 20:1) to obtain 3-(2-acetamidoethyl)-5-methoxy-N-methyl-1H-indole-2-carboxamide (80.0 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble materials were separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 20:1)

Sources & evidence

ORD record
ord-a186057393724932bc342bb4d60285b1
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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