Diisopropylethylamine → HCID 72948198, compound

HRID 2207754Notes

Reaction equation

HRID 2207754 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([F:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C:8]=1[C:19]([OH:21])=O)(=[O:3])[CH3:2].[CH:22]([N:25](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][C:12]([F:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C:8]=1[C:19]([NH:25][CH3:22])=[O:21])(=[O:3])[CH3:2]

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 89933016HCID 89933016, compound

Product 1

HCID 72948198HCID 72948198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(2-acetamidoethyl)-6-fluoro-5-methoxy-1H-indole-2-carboxylic acid (2.11 g), diisopropylethylamine (6.14 mL), methylamine hydrochloride (1.45 g), and N,N-dimethyl formamide (42.2 mL) was added 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (6.82 g), followed by stirring at room temperature overnight. To the mixture was added ice water, followed by extraction with ethyl acetate and further extraction with chloroform/methanol (10:1). 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 10:1) to obtain 3-(2-acetamidoethyl)-6-fluoro-5-methoxy-N-methyl-1H-indole-2-carboxamide (1.64 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate and further extraction with chloroform/methanol (10:1)
  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 10:1)

Sources & evidence

ORD record
ord-4c2fe434d39d4b9d84d6ef841dca1dda
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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