3,4-Dimethoxyaniline → HCID 25265258, compound

HRID 450515Notes

Reaction equation

HRID 450515 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[N:11]=[N:10]2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[NH2:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:23][C:15]([C:12]2[N:11]=[N:10][N:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:13]=2[CH3:14])=[O:17])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

6

Reactant 4

HCID 227703,4-DimethoxyanilineHCID 81531DiisopropylethylamineHCID 27645811-[(4-Fluorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid, 4-Carboxy-1-(4-fluorobenzyl)-5-methyl-1H-1,2,3-triazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 25265258HCID 25265258, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[(4-fluorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (0.2 g, 0.85 mmol), 3,4-bis(methyloxy)aniline (0.156 g, 1.2 eq), HATU (0.485 g, 1.5 eq) and DIPEA (240 μL, 1.5 eq) in DMF was stirred at room temperature overnight. The solvent was evaporated and the residue was washed with water and extracted with DCM. The organic phase was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with DCM to give after precipitation from ether, the title compound as a white solid (180 mg, 57%). HRMS calculated for C19H19FN4O3 (M+H)+371.1519, found: 371.1500, Rt: 2.78 min. MP: 119.7° C.

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography
  8. washeluting with DCM
  9. customto give
  10. customafter precipitation from ether

Sources & evidence

ORD record
ord-bfbcc686685647e0b0289f568415b89a
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

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