Dipropylamine → HCID 86659888, compound

HRID 2360167Notes

Reaction equation

HRID 2360167 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([OH:14])=O)=[CH:6]2.[CH2:15]([NH:18][CH2:19][CH2:20][CH3:21])[CH2:16][CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.C(OCC)C>[CH2:15]([N:18]([CH2:19][CH2:20][CH3:21])[C:12]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)=[O:14])[CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 204015-Methoxyindole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86659888HCID 86659888, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methoxyindole-2-carboxylic acid (500 mg, 2.62 mmol) in 13 mL of N,N-dimethylformamide was added di-n-propylamine (1.07 mL, 7.8 mmol) and HATU (1.09 g, 2.88 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 12 h, the reaction mixture was diluted with diethyl ether, and washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography to obtain the title compound (0.53 g, 74%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c42f36d5f7df4ff3828a721200b321e8
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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