Diisopropylethylamine → HCID 44540686, compound

HRID 1616004Notes

Reaction equation

HRID 1616004 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][CH:6]=1)[CH3:3].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:47]1[C:55]2[C:50](=[C:51]([C:56]3[CH:57]=[C:58]([NH2:71])[C:59]4[C:63]([CH:64]=3)=[N:62][N:61](C3CCCCO3)[CH:60]=4)[CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:3][N:2]([CH2:4][C:5]1[N:10]=[C:9]([C:11]([NH:71][C:58]2[CH:57]=[C:56]([C:51]3[CH:52]=[CH:53][CH:54]=[C:55]4[C:50]=3[CH:49]=[CH:48][NH:47]4)[CH:64]=[C:63]3[C:59]=2[CH:60]=[N:61][NH:62]3)=[O:13])[CH:8]=[CH:7][CH:6]=1)[CH3:1]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amineHCID 58268028HCID 58268028, compound

Product 1

HCID 44540686HCID 44540686, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-[(dimethylamino)methyl]-2-pyridinecarboxylic acid (27 mg, 0.15 mmol) in DMF (0.0008 ml) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (72 mg, 0.19 mmol) and DIPEA (0.052 ml). After 5 minutes the resulting solution was added to 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (33 mg, 0.10 mmol). After stirring for 90 mins at room temperature the mixture was treated with saturated sodium bicarbonate solution (10 ml) and extracted with dichloromethane (3×10 ml). The extracts were passed through a hydrophobic frit, combined and the solvent was evaporated under nitrogen flow. The residue was dissolved in methanol (2 ml) and hydrochloric acid (2M, 0.080 ml) was added. The solvents were evaporated under nitrogen stream to give a crude product which was purified by Mass Directed Automated Preparative HPLC (Method B). Fractions containing pure product were evaporated under a nitrogen stream to give the title compound (22 mg) as a pale solid.

Workup

  1. extractionextracted with dichloromethane (3×10 ml)
  2. customthe solvent was evaporated under nitrogen flow
  3. dissolutionThe residue was dissolved in methanol (2 ml)
  4. additionhydrochloric acid (2M, 0.080 ml) was added
  5. customThe solvents were evaporated under nitrogen stream
  6. customto give a crude product which
  7. customwas purified by Mass Directed Automated Preparative HPLC (Method B)
  8. additionFractions containing pure product
  9. customwere evaporated under a nitrogen stream

Sources & evidence

ORD record
ord-f0625fe98fe243f1a9901c7254e8246a
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

Loading…