Triethylamine → HCID 67021641, compound

HRID 1660979Notes

Reaction equation

HRID 1660979 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:20])[C:17]([OH:19])=O)=[CH:12][CH:11]=2)[CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[C:52]([C:56]1[CH:57]=[C:58]([NH2:68])[N:59]([C:61]2[CH:66]=[CH:65][C:64]([CH3:67])=[CH:63][CH:62]=2)[N:60]=1)([CH3:55])([CH3:54])[CH3:53]>CN(C=O)C>[C:52]([C:56]1[CH:57]=[C:58]([NH:68][C:17](=[O:19])[C:16]([C:13]2[CH:12]=[CH:11][C:10]([N:3]3[C:4]4=[N:5][CH:6]=[CH:7][CH:8]=[C:9]4[N:1]=[CH:2]3)=[CH:15][CH:14]=2)=[O:20])[N:59]([C:61]2[CH:62]=[CH:63][C:64]([CH3:67])=[CH:65][CH:66]=2)[N:60]=1)([CH3:55])([CH3:54])[CH3:53]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)3×HCID 67021597HCID 67021597, compound

Product 1

HCID 67021641HCID 67021641, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4-imidazo[4,5-b]pyridine-3-yl-phenyl)-oxo-acetic acid, HATU (104 mg, 0.27 mmol, 1.1 equiv) and triethylamine (0.102 mL, 0.73 mmol) in DMF (4 mL) is stirred for 5 minutes under N2. 5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-ylamine is then added and after 2 h, a further 1.2 equiv of HATU is added and after a further 2 h an additional 1.2 equiv of HATU is added. After 4 h, DMF is removed and the residue taken up in EtOAc and washed with 1N HCl, 1N NaOH and finally with brine. The organic layer is dried with MgSO4, filtered and concentrated. The residue is purified by MPLC on reverse phase with ACN/water to give N-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-2-oxo-acetamide as a yellow oil. Title compound: 479.05 [M+H]+; tR=1.9 min (System 2).

Workup

  1. additionis added
  2. customDMF is removed
  3. washwashed with 1N HCl, 1N NaOH and finally with brine
  4. dry with materialThe organic layer is dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by MPLC on reverse phase with ACN/water

Sources & evidence

ORD record
ord-7d54b0b701af43fb968d147d9e65b67e
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

Loading…