Diethylamine → HCID 58045805, compound

HRID 657901Notes

Reaction equation

HRID 657901 reaction equation
Cl.[NH2:2][C:3]1[N:7]2[N:8]=[C:9]([C:13]([OH:15])=O)[CH:10]=[C:11]([CH3:12])[C:6]2=[N:5][N:4]=1.F[B-](F)(F)F.C(OC([C:26](=NOC(N(C)C)=[N+](C)C)[C:27]#[N:28])=O)C.C(NCC)C>CN(C=O)C>[CH2:27]([NH:28][C:13]([C:9]1[CH:10]=[C:11]([CH3:12])[C:6]2[N:7]([C:3]([NH2:2])=[N:4][N:5]=2)[N:8]=1)=[O:15])[CH3:26]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66941571HCID 66941571, compound

Product 1

HCID 58045805HCID 58045805, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Amino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylic acid hydrochloride (W1.141; 300 mg) was dissolved in DMF (6 ml) and admixed with O-[(ethoxycarbonyl)-cyanomethyleneamino]-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TOTU; 429 mg) and diethylamine (573 mg). After 2 h, the DMF was drawn off and the residue was purified using silica gel (24 g cartridge, dichloromethane/methanol gradient of 0-20% in 60 min). The product was taken up with water and freeze-dried. In order to remove residual diethylamine, the mixture was chromatographed using a short column (dichloromethane/methanol 95:5). 112 mg of the title compound were obtained, which was still contaminated with diethylamine.

Workup

  1. customthe residue was purified
  2. customsilica gel (24 g cartridge, dichloromethane/methanol gradient of 0-20% in 60 min)
  3. customfreeze-dried
  4. customIn order to remove residual diethylamine
  5. customthe mixture was chromatographed

Sources & evidence

ORD record
ord-1f181d9d03aa42788c3d8e5ee5220044
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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