Diisopropylethylamine → HCID 44541051, compound

HRID 1616024Notes

Reaction equation

HRID 1616024 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.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>[F: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 2260276-Fluoropyridine-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 44541051HCID 44541051, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-Fluoro-2-pyridinecarboxylic acid (available from Asymchem Laboratories, 570 mg, 4.0 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1531 mg, 4.0 mmol) were dissolved in DMF (15 ml) and treated with DIPEA (2.11 ml). The mixture was stirred at room temperature for 30 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (500 mg, 2.0 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to approx. 5 ml which was added to 2×50 g aminopropyl cartridges that had been preconditioned with MeOH. The reaction mixture remained on the cartridges for 2 h before being eluted with MeOH. The mixture was concentrated in vacuo to give an orange oil. DCM (5 ml) was added and the resultant precipitate was collected by filtration to give the title compound (235 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 which
  3. additionwas added to 2×50 g aminopropyl cartridges that
  4. waitThe reaction mixture remained on the cartridges for 2 h
  5. washbefore being eluted with MeOH
  6. concentrationThe mixture was concentrated in vacuo
  7. customto give an orange oil
  8. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-0ec36868ab334dd9ab05cc8dd836109e
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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