Dimethylformamide → HCID 68683806, compound

HRID 2234523Notes

Reaction equation

HRID 2234523 reaction equation
[CH2:1]([N:3]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])[CH3:5])C.[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][C:12]=1[O:20][CH3:21].[CH3:22][N:23](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=[O:50])C>>[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:23][CH:22]2[CH2:6][C@H:4]3[N:3]([CH3:1])[C@H:7]([CH2:9][O:50][CH2:5]3)[CH2:8]2)=[O:16])=[CH:13][C:12]=1[O:20][CH3:21]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2880572486-69-3HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68683806HCID 68683806, compoundYield 98%

Procedure

N-Ethyldiisopropylamine (0.119 mL, 0.68 mmol) was added to 4-amino-3-methoxybenzoic acid (Aldrich; 114 mg, 0.68 mmol), (1R,5S,7s)-9-methyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-amine (Bioorganic & Medicinal Chemistry Letters (1992), 2(6), 519-22, 107 mg, 0.68 mmol) and HATU (260 mg, 0.68 mmol) in DMF (5 mL) at 25° C. The resulting solution was stirred at ambient temperature for 6 hours. The DMF was evaporated to give a brown gum as residue, which was purified by ion exchange chromatography, using an SCX-2 (5 g) column pre-wet with methanol. The desired product was eluted from the column using 2M NH3/MeOH and purified fractions were evaporated to dryness to afford a brown gum which was purified by flash silica chromatography, elution gradient 0 to 100% 5% MeOH/DCM in DCM. Pure fractions were combined and evaporated to dryness to afford the title compound as a beige coloured gum (205 mg, 98%).

Workup

  1. customThe DMF was evaporated
  2. customto give a brown gum as residue
  3. customwhich was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. custompurified fractions
  6. customwere evaporated to dryness
  7. customto afford a brown gum which
  8. customwas purified by flash silica chromatography, elution gradient 0 to 100% 5% MeOH/DCM in DCM
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-5fdfb15a7da747fc950233a1d0908623
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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