Diisopropylethylamine → HCID 58049384, compound

HRID 467953

Reaction equation

HRID 467953 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][CH2:8][CH2:9][OH:10])[CH2:3][CH2:2]1.[CH3:11][N:12]1[CH:16]=[C:15]([C:17](O)=[O:18])[N:14]=[CH:13]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(#N)C>[OH:10][CH2:9][CH2:8][N:7]([CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:17]([C:15]1[N:14]=[CH:13][N:12]([CH3:11])[CH:16]=1)=[O:18]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 235372252-[(TETRAHYDRO-2H-PYRAN-4-YL)AMINO]ETHANOL

Product 1

HCID 58049384HCID 58049384, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(tetrahydro-2H-pyran-4-ylamino)ethanol (3.45 g), 1-methyl-1H-imidazole-4-carboxylic acid (3.00 g), HATU (13.6 g), diisopropylethylamine (12.4 mL) and acetonitrile (52 mL) was stirred at room temperature for 2 hours. The solvents were distilled off under reduced pressure and the resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=98:2 to 96:4) to give the titled compound (2.34 g).

Workup

  1. distillationThe solvents were distilled off under reduced pressure
  2. customthe resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=98:2 to 96:4)

Sources & evidence

ORD record
ord-58921a424fca43348ccd04e8f98af185
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Linked notes

Loading…