Methylamine → HCID 42606323, compound

HRID 222374Notes

Reaction equation

HRID 222374 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[S:20][C:21]([C:25](O)=[O:26])=[C:22]([CH3:24])[N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CN.[CH3:30][N:31](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>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[S:20][C:21]([C:25]([NH:31][CH3:30])=[O:26])=[C:22]([CH3:24])[N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 42606209HCID 42606209, compound

Product 1

HCID 42606323HCID 42606323, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-4-methyl-1,3-thiazole-5-carboxylic acid (Example 16) (0.15 g, 0.35 mmol), methylamine (96 μL, 2.46 mmol), HATU (0.268 g, 0.70 mmol) and DIPEA (80 μL, 0.46 mmol) in DMF was stirred at 40° C. overnight. The solvent was evaporated and the residue was washed with water and extracted with DCM (large volume). The organic phase was dried over sodium sulphate, filtered and concentrated. The residue was twice purified by flash chromatography eluting with DCM/MeOH (95/5) to give after crystallisation from ether the title compound as a white solid (33 mg, 21%). HRMS calculated for C17H16Cl2N6O2S (M+H)+439.0511, found: 439.0548, Rt: 2.69 min. MP: 218.5° C.

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with water
  3. extractionextracted with DCM (large volume)
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was twice purified by flash chromatography
  8. washeluting with DCM/MeOH (95/5)
  9. customto give
  10. customafter crystallisation from ether the title compound as a white solid (33 mg, 21%)

Sources & evidence

ORD record
ord-e2b54b31b5e74cc78626b382ef3022c0
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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