Diisopropylethylamine → HCID 118074746, compound

HRID 1775430Notes

Reaction equation

HRID 1775430 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=2)[NH:13][C:12]=1[C:22](O)=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:25]([N:28](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>[CH3:21][O:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:22](=[O:23])[NH:28][CH3:25])=[C:11]2[CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118071488HCID 118071488, compound

Product 1

HCID 118074746HCID 118074746, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-{2-[(tert-butoxycarbonyl)amino]ethyl}-5-methoxy-1H-indole-2-carboxylic acid (500 mg), diisopropylethylamine (1.28 mL), methylamine hydrochloride (303 mg), and N,N-dimethyl formamide (10.0 mL) was added 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (853 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 the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 20:1) to obtain tert-butyl {2-[5-methoxy-2-(methylcarbamoyl)-1H-indol-3-yl]ethyl}carbamate (520 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-84f3180c25dd48609d61bce7c51e37d3
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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