Methylamine → HCID 56603144, compound

HRID 1809439Notes

Reaction equation

HRID 1809439 reaction equation
CN.[CH3:3][C:4]([C:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:28])[C:16]([CH3:27])([S:18]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH3:17])[O:11][N:10]=1)([CH3:8])[C:5](O)=[O:6].F[P-](F)(F)(F)(F)F.[N:36]1(OC(N(C)C)=[N+](C)C)[C:40]2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH3:17][C:16]([S:18]([CH:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)(=[O:19])=[O:20])([CH3:27])[C:15]([NH:14][C:12]1[O:11][N:10]=[C:9]([C:4]([CH3:8])([C:5](=[O:6])[NH:36][CH3:40])[CH3:3])[CH:13]=1)=[O:28]

Participants

7

Reactant 4

HCID 6329Methylamine2×HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 56602957HCID 56602957, compound

Product 1

HCID 56603144HCID 56603144, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2 Methyl amine (2M solution in THF, 0.125 mL, 0.25 mmol) is added to a solution of 2-Methyl-2-{5-[2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionylamino]-isoxazol-3-yl}-propionic acid (50 mg, 0.13 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (57 mg, 0.15 mmol) in DMF (1 mL), followed by the addition of N,N-diisopropylethylamine (0.056 mL, 0.32 mmol). The reaction mixture is stirred at room temperature for 65 h. After this time, more O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (100 mg, 0.26 mmol) and methylamine (2M solution in THF, 0.125 mL, 0.25 mmol) are added to the reaction mixture. The reaction mixture is stirred for 1 hour at room temperature. After this time, the reaction mixture is diluted with water and extracted with ethyl acetate twice. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by preparative LC-MS affords 12 mg of the title compound. Yield: 23%; m/z 402 [M+H].

Workup

  1. stirringThe reaction mixture is stirred for 1 hour at room temperature
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative LC-MS

Sources & evidence

ORD record
ord-40edfe9b8fe0460f82bf28a4dde61b32
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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