Ammonia → HCID 44540892, compound

HRID 244721Notes

Reaction equation

HRID 244721 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([OH:8])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[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.CCN(C(C)C)C(C)C.N>CN(C=O)C.CO>[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:2]4[NH:1][CH:5]=[CH:4][N:3]=4)=[O:8])[CH:43]=3)[CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 5743211H-Imidazole-2-carboxylic acidHCID 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-amine

Product 1

HCID 44540892HCID 44540892, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

1H-Imidazole-2-carboxylic acid (17 mg) (available from Maybridge), HATU (63 mg) and 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (50 mg) were dissolved in anhydrous DMF (3 ml) and then treated with DIPEA (0.052 ml) and stirred at RT for 15 h. The mixture was treated with methanol (3 ml) and then macroporous-tosic acid resin (170 mg; 4.4 mmol/g) then stirred for 15 h. The mixture was then treated with 0.88 ammonia solution (0.600 ml), stirred for 10 min, then filtered and solvent blown off under a stream of nitrogen. The crude residue was purified by mass directed preparative HPLC (Method A) to give the title compound.

Workup

  1. stirringstirred for 10 min
  2. filtrationfiltered
  3. customThe crude residue was purified by mass

Sources & evidence

ORD record
ord-1d9ce1e3f37046009054511e2b7b72ca
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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