4-Aminopyridine → HCID 67411147, compound

HRID 1403675Notes

Reaction equation

HRID 1403675 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]([OH:7])=O.[NH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O.CN(C1C=CN=CC=1)C>[C:16]([O:15][C:13](=[O:14])[NH:12][CH2:11][C:10]1[CH:9]=[CH:8][C:4]([C:5](=[O:7])[NH:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:3][C:2]=1[Br:1])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67411497HCID 67411497, compound

Product 1

HCID 67411147HCID 67411147, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of Intermediate 15 (100 g, 0.303 mol, 1.0 eq) and 4-aminopyridine (28.5 g, 0.303 mol, 1.0 eq) in DMA (1 L) was added Et3N (30.6 g, 0.303 mol, 1.0 eq), DMAP (3.7 g, 0.030 mol, 0.1 eq) and HATU (115.2 g, 0.303 mol, 1.0 eq). The reaction solution was stirred at 30° C. for 16 hrs. Solvent was evaporated under vacuum and the residue was solidified by adding DCM (600 ml) and H2O (600 ml) to give the title compound (86.1 g, 70% yield).

Workup

  1. customSolvent was evaporated under vacuum
  2. additionby adding DCM (600 ml) and H2O (600 ml)

Sources & evidence

ORD record
ord-cd9f5d14b81a470ba1aff0330f9ceec1
Source dataset
uspto-grants-2014_12
Patent number
US08912209B2

Reaction notes

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