Methylamine → HCID 76285219, compound

HRID 1770667Notes

Reaction equation

HRID 1770667 reaction equation
[CH2:1]([S:3][C:4]1[C:13]([C:14]([OH:16])=O)=[C:12]([CH3:17])[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:2].CN(C(ON1N=N[C:28]2[CH:29]=[CH:30][CH:31]=[N:32][C:27]1=2)=[N+](C)C)C.[F:35][P-](F)(F)(F)(F)F.CN.[CH2:44]1[CH2:48]OCC1>>[CH2:1]([S:3][C:4]1[C:13]([C:14]([NH:32][CH2:31][C:30]2[CH:44]=[CH:48][CH:27]=[C:28]([F:35])[CH:29]=2)=[O:16])=[C:12]([CH3:17])[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:2]

Participants

5

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86720179HCID 86720179, compound

Product 1

HCID 76285219HCID 76285219, compoundYield 50%

Procedure

To a solution of 2-(ethylthio)-4-methyl-1,7-naphthyridine-3-carboxylic acid (0.25 g, 1.01 mmol, 1 eq) in dry THF (12 ml) were added HATU (0.42 g, 1.11 mmol, 1.1 eq) and TEA (0.4 ml, 3.03 mmol, 3 eq) at RT and the reaction mixture was stirred at RT for 15 min. 3-fluorophenyl)methanamine (0.16 g, 1.26 mmol, 1.25 eq) was added to the mixture at RT and the reaction mixture was stirred at RT for 1 h. Afterwards the excess solvent was distilled off and the residue was diluted with a sat. aq. solution of NH4Cl (50 ml). The aq. part was extracted with EtOAc (3×80 ml). The combined organic layers were washed with a sat. aq. solution of NaHCO3 (50 ml), water (50 ml), dried over anhydrous Na2SO4 and evaporated to provide the crude product, which was purified by CC (acetone/hexane 2:9) to yield 2-Ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-[1,7]naphthyridine-3-carboxylic acid amide (example 2) (0.18 g, 0.51 mmol, 50%). MS m/z [M+H]+ 356.1.

Workup

  1. stirringthe reaction mixture was stirred at RT for 1 h
  2. distillationAfterwards the excess solvent was distilled off
  3. additionthe residue was diluted with a sat. aq. solution of NH4Cl (50 ml)
  4. extractionThe aq. part was extracted with EtOAc (3×80 ml)
  5. washThe combined organic layers were washed with a sat. aq. solution of NaHCO3 (50 ml), water (50 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated
  8. customto provide the crude product, which
  9. customwas purified by CC (acetone/hexane 2:9)

Sources & evidence

ORD record
ord-f19f4e6870b245afb89d32a81962506c
Source dataset
uspto-grants-2016_02
Patent number
US09248122B2

Reaction notes

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