Diisopropylethylamine → HCID 72948198, compound

HRID 1775458Notes

Reaction equation

HRID 1775458 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-112390b774744d5baa928b2970cc4a69
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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