Diisopropylethylamine → HCID 44540317, compound

HRID 1616046Notes

Reaction equation

HRID 1616046 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:44]1[C:52]2[C:47](=[C:48]([C:53]3[CH:54]=[C:55]([NH2:62])[C:56]4[CH:57]=[N:58][NH:59][C:60]=4[CH:61]=3)[CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45]1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:62][C:55]2[CH:54]=[C:53]([C:48]3[CH:49]=[CH:50][CH:51]=[C:52]4[C:47]=3[CH:46]=[CH:45][NH:44]4)[CH:61]=[C:60]3[C:56]=2[CH:57]=[N:58][NH:59]3)=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6085445-Bromopyridine-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 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 44540317HCID 44540317, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-2-pyridinecarboxylic acid (980 mg, 4.83 mmol, available from Alfa Aesar) in DMF (15 ml) was added HATU (1840 mg, 4.83 mmol) and DIPEA (2.53 ml, 14.50 mmol). The mixture was stirred at room temperature for 30 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (600 mg, 2.41 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to approx. 5 ml volume and was applied to 2×50 g aminopropyl cartridges that had been pre-conditioned with MeOH. The reaction mixture remained on the cartridges for 2 h before being eluted with MeOH. The eluent was concentrated in vacuo and a precipitate formed, which was collected by filtration to give the title compound (430 mg) as a yellow solid.

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo to approx. 5 ml volume
  3. waitThe reaction mixture remained on the cartridges for 2 h
  4. washbefore being eluted with MeOH
  5. concentrationThe eluent was concentrated in vacuo
  6. customa precipitate formed
  7. filtrationwhich was collected by filtration

Sources & evidence

ORD record
ord-a200f78a3806479c87cfb28b600280f6
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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