Diisopropylethylamine → HCID 44539831, compound

HRID 1616036Notes

Reaction equation

HRID 1616036 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=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.C(Cl)Cl.CO>[NH2:1][C:2]1[N:7]=[C:6]([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])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 3516526-Aminopyridine-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 44539831HCID 44539831, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 6-amino-2-pyridinecarboxylic acid (120 mg, 0.89 mmol, available from Apollo Scientific) in DMF (2 ml) was added HATU (340 mg, 0.89 mmol) and DIPEA (0.464 ml, 2.67 mmol). The mixture was stirred at room temperature for 20 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (110 mg, 0.44 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was applied to the top of a 50 g aminopropyl cartridge that had been preconditioned with DCM/MeOH (1:1). The reaction mixture remained on the cartridges for 2 h before being eluted with DCM/MeOH (1:1). The solvent was removed in vacuo to give a brown oil that was purified by chromatography using silica gel (50 g cartridge, FlashMaster II) eluting with 0-100% ethyl acetate in cyclohexane over 30 mins followed by 0-20% MeOH in ethyl acetate over 10 mins to afford the title compound (26 mg) as a pale yellow gum.

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. waitThe reaction mixture remained on the cartridges for 2 h
  3. washbefore being eluted with DCM/MeOH (1:1)
  4. customThe solvent was removed in vacuo
  5. customto give a brown oil that
  6. customwas purified by chromatography
  7. washeluting with 0-100% ethyl acetate in cyclohexane over 30 mins
  8. waitfollowed by 0-20% MeOH in ethyl acetate over 10 mins

Sources & evidence

ORD record
ord-e3b4513d042a4392ae2d602a2e8659ab
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

Loading…