Propiolic Acid → HCID 57708572, compound

HRID 2391540Notes

Reaction equation

HRID 2391540 reaction equation
[C:1](O)(=[O:4])[C:2]#[CH:3].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:21][C:22]1[CH:23]=[C:24]([CH:41]=[CH:42][CH:43]=1)[O:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([CH:32]=[C:33]([NH:35][C:36]([CH:38]3[CH2:40][CH2:39]3)=[O:37])[N:34]=2)[N:31]=1>O1CCCC1.CN(C)C=O>[C:1]([NH:21][C:22]1[CH:23]=[C:24]([CH:41]=[CH:42][CH:43]=1)[O:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([CH:32]=[C:33]([NH:35][C:36]([CH:38]3[CH2:40][CH2:39]3)=[O:37])[N:34]=2)[N:31]=1)(=[O:4])[C:2]#[CH:3]

Participants

6

Reactant 3

HCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57708572HCID 57708572, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of propiolic acid (27 mg, 0.387 mmol) in tetrahydrofuran (2 mL) and N,N-dimethylformamide (2 mL) was added N,N′-dicyclohexylcarbodiimide (100 mg, 0.484 mmol) under ice-cooling, and the mixture was stirred for 30 min. To the reaction mixture was added N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (100 mg, 0.323 mmol), and the mixture was stirred under ice-cooling for 4 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→100/0) to give the title compound (24 mg, 21%) as a pale-orange powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 4 hr
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→100/0)

Sources & evidence

ORD record
ord-ea93a2ee113344f2bf3ceb3ea1c74e1a
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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