Methylamine → US9777003, Example 82

HRID 628338Notes

Reaction equation

HRID 628338 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:15]1[C:19]2[CH:20]=[CH:21][C:22]3[N:23]([C:24]([CH3:27])=[N:25][N:26]=3)[C:18]=2[CH:17]=[C:16]1[C:28](O)=[O:29])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:31]([N:34](CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN.C1COCC1>CN(C=O)C.CO>[CH2:8]([N:15]1[C:19]2[CH:20]=[CH:21][C:22]3[N:23]([C:24]([CH3:27])=[N:25][N:26]=3)[C:18]=2[CH:17]=[C:16]1[C:28]([NH:34][CH3:31])=[O:29])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1181594706-benzyl-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid trifluoroacetate

Product 1

HCID 118159766US9777003, Example 82

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-benzyl-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid trifluoroacetate (0.044 g, 0.10 mmol, from Step 4) in DMF (1 mL) was added N,N-diisopropylethylamine (0.17 mL, 0.98 mmol) followed by N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.14 g, 0.37 mmol). After stirring this combination for 2 minutes, 2.0 M methylamine in THF (0.42 mL, 0.84 mmol) was added. After a reaction time of 15 minutes, the reaction was diluted with MeOH, and the product was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH) (0.03 g, 90%).

Workup

  1. customthe product was purified via preparative HPLC-MS (C18
  2. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH) (0.03 g, 90%)

Sources & evidence

ORD record
ord-b44282ba15e242c6bde23d6fafb4d660
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

Loading…