Diisopropylethylamine → HCID 44539630, compound

HRID 1616039Notes

Reaction equation

HRID 1616039 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.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.CS(C)=O.CO.CO>[NH:44]1[C:52]2[C:47](=[C:48]([C:53]3[CH:61]=[C:60]4[C:56]([CH:57]=[N:58][NH:59]4)=[C:55]([NH:62][C:4]([C:3]4[C:2]([CH3:1])=[N:10][CH:9]=[CH:8][CH:7]=4)=[O:6])[CH:54]=3)[CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 6433732-Methylnicotinic 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 44539630HCID 44539630, compoundYield 25.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

To a solution of 2-methylnicotinic acid (55 mg, 0.40 mmol) in DMF (2 ml) was added HATU (150 mg, 0.40 mmol) and DIPEA (0.211 ml, 1.21 mmol). The mixture was stirred at room temperature for 20 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg, 0.20 mmol) was added and the mixture was stirred at room temperature for 18 h. The reaction mixture was added to the top of a 20 g aminopropyl cartridge that had been pre-conditioned with MeOH. The reaction mixture remained on the cartridges for 3 h before being eluted with MeOH. The solvent was removed in vacuo to give a crude residue that was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method E). The sample was further purified using Mass Directed Automated Preparative HPLC (Method E) and product-containing fractions were dried under a stream of nitrogen to give the title compound (19 mg) as a pale yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. additionThe reaction mixture was added to the top of a 20 g aminopropyl cartridge that
  3. waitThe reaction mixture remained on the cartridges for 3 h
  4. washbefore being eluted with MeOH
  5. customThe solvent was removed in vacuo
  6. customto give a crude residue that
  7. custompurified by Mass Directed Automated Preparative HPLC (Method E)
  8. customThe sample was further purified
  9. additionproduct-containing fractions
  10. customwere dried under a stream of nitrogen

Sources & evidence

ORD record
ord-1d584e8e23064113aac25108872326ee
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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