Diisopropylethylamine → HCID 178508301, compound

HRID 2264221Notes

Reaction equation

HRID 2264221 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([OH:8])=O)=[N:2]1.F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C.C(N(C(C)C)C(C)C)C.[F:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][C:48]=1[C:49]1[C:50]([C:57]2[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=2)=[N:51][C:52]([NH2:56])=[C:53]([NH2:55])[CH:54]=1>CN(C=O)C>[NH2:56][C:52]1[N:51]=[C:50]([C:57]2[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=2)[C:49]([C:48]2[CH:47]=[CH:46][N:45]=[CH:44][C:43]=2[F:42])=[CH:54][C:53]=1[NH:55][C:6]([C:3]1[N:4]=[CH:5][NH:1][N:2]=1)=[O:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595959543''-Fluoro-3,2':3',4''-terpyridine-5',6'-diamine2×HCID 178524907HCID 178524907, compound

Product 1

HCID 178508301HCID 178508301, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1H-1,2,4-triazole-3-carboxylic acid (0.072 g, 0.64 mmol), N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate (0.243 g, 0.64 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.205 mL, 1.17 mmol) in DMF (1.5 mL) was stirred for 15 minutes under argon. Finally, 3″-fluoro-3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 1, 0.15 g, 0.53 mmol) in DMF (3 mL) was added and the mixture was stirred at room temperature for 20 hours. The solvent was evaporated and the crude mixture was purified by silica gel flash chromatography (90:10 dichloromethane/methanol) to give the title compound (0.070 g, 35% of yield).

Workup

  1. customThe solvent was evaporated
  2. customthe crude mixture was purified by silica gel flash chromatography (90:10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-45c0cb46b2ac4f2e8bf97b724828e2d2
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

Loading…