Methylamine → HCID 57525008, compound

HRID 1477832Notes

Reaction equation

HRID 1477832 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)[C:12]2N=CC=CC=2N=N1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C@:32]([N:38]2[C:46]3[C:41](=[C:42]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39]2)([CH2:36][CH3:37])[C:33]([OH:35])=O)=[CH:28][CH:27]=1.CN1CCOCC1.CN>CN(C=O)C.CO>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C@:32]([N:38]2[C:46]3[C:41](=[C:42]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39]2)([CH2:36][CH3:37])[C:33]([NH:8][CH3:12])=[O:35])=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68175254HCID 68175254, compound

Product 1

HCID 57525008HCID 57525008, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.34 g, 3.56 mmol) was added to a stirred solution of 4a (967 mg, 2.38 mmol) and 4-methylmorpholine (523 μL, 4.75 mmol) in DMF (12 mL). After 5 min, methylamine (3.56 mL of a 2.0 M solution in methanol, 7.13 mmol) was added, and the resulting mixture was allowed to stir at rt. After 3 h, the reaction mixture was partitioned between ethyl acetate and water. The layers were separated, and the organics were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-85% EtOAc/hexanes as eluent) to afford the title compound 39. m/z (ES) 420 (MH)+; IP=B rating.

Workup

  1. waitAfter 3 h
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organics were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-85% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-50d3a459349441a29456d6be7c4744da
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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