Diisopropylethylamine → HCID 44539732, compound

HRID 1616035Notes

Reaction equation

HRID 1616035 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH: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.CO>[Cl:1][C:2]1[C:3]([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:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 8246323-Chloropyridine-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 44539732HCID 44539732, compoundYield 27.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloropicolinic acid (380 mg, 2.42 mmol, available from Fluorochem Ltd.) in DMF (5 ml) was added HATU (920 mg, 2.42 mmol) and DIPEA (1.266 ml, 7.25 mmol). The mixture was stirred at room temperature for 20 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (300 mg, 1.21 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to give a volume of approx. 1 ml which was added to the top of a 20 g aminopropyl cartridge that had been preconditioned with MeOH. The reaction mixture remained on the cartridges for 2 h before being eluted with MeOH. The solvent was removed in vacuo to give a brown oil that was purified by chromatography using silica gel (70 g cartridge, FlashMaster II) eluting with 0-25% MeOH in DCM over 30 mins to afford the title compound (130 mg) as a brown solid.

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a volume of approx. 1 ml which
  4. additionwas added to the top of a 20 g aminopropyl cartridge that
  5. waitThe reaction mixture remained on the cartridges for 2 h
  6. washbefore being eluted with MeOH
  7. customThe solvent was removed in vacuo
  8. customto give a brown oil that
  9. customwas purified by chromatography
  10. washeluting with 0-25% MeOH in DCM over 30 mins

Sources & evidence

ORD record
ord-51aadf96b9534bccae5ca942a229222b
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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