Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178521746, compound

HRID 244719Notes

Reaction equation

HRID 244719 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.F[P-](F)(F)(F)(F)F.CN(C(ON1C2=NC=CC=C2N=N1)=[N+](C)C)C.[NH:33]1[C:41]2[C:36](=[C:37]([C:42]3[CH:43]=[C:44]([NH2:57])[C:45]4[C:49]([CH:50]=3)=[N:48][N:47](C3CCCCO3)[CH:46]=4)[CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34]1>CN(C=O)C.CCN(C(C)C)C(C)C>[NH:33]1[C:41]2[C:36](=[C:37]([C:42]3[CH:50]=[C:49]4[C:45]([CH:46]=[N:47][NH:48]4)=[C:44]([NH:57][C:6]([C:4]4[N:3]=[CH:2][NH:1][CH:5]=4)=[O:8])[CH:43]=3)[CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34]1

Participants

6

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amineHCID 178524800HCID 178524800, compound

Product 1

HCID 178521746HCID 178521746, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 81531DiisopropylethylamineSolvent

Procedure

1H-Imidazole-4-carboxylic acid (7 mg) in DMF (0.2 ml) was treated with N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (27 mg) in DMF (0.2 ml) and DIPEA (0.03 ml). The reaction mixture was shaken for five min prior to treatment with 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (20 mg) in DMF (0.2 ml). The reaction mixture was shaken for five min and left to stand at 22° C. for 18 h. Solvent was removed in vacuo and the product re-dissolved in methanol (0.5 ml) prior to application on to an SCX SPE cartridge (1 g). The product was eluted after 1 h with 2M ammonia in methanol (2×3 ml), the fractions were combined and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method C) gave the title compound.

Workup

  1. stirringThe reaction mixture was shaken for five min
  2. waitleft
  3. waitto stand at 22° C. for 18 h
  4. customSolvent was removed in vacuo
  5. dissolutionthe product re-dissolved in methanol (0.5 ml)
  6. washThe product was eluted after 1 h with 2M ammonia in methanol (2×3 ml)
  7. concentrationconcentrated under a stream of nitrogen using blow down apparatus
  8. customPurification by mass

Sources & evidence

ORD record
ord-dbf696276dfd41699a0ade5a305be2c6
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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