Hydrochloric Acid → HCID 69920753, compound

HRID 1634208Notes

Reaction equation

HRID 1634208 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C[Al](C)C.CO[C:12]([C:14]1[CH:19]=[C:18]([NH2:20])[N:17]2[N:21]=[C:22]([C:24]3[O:25][C:26]([CH3:29])=[CH:27][CH:28]=3)[N:23]=[C:16]2[CH:15]=1)=[O:13].Cl>O1CCOCC1>[CH2:1]([N:3]([CH2:4][CH3:5])[C:12]([C:14]1[CH:19]=[C:18]([NH2:20])[N:17]2[N:21]=[C:22]([C:24]3[O:25][C:26]([CH3:29])=[CH:27][CH:28]=3)[N:23]=[C:16]2[CH:15]=1)=[O:13])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 16682925TrimethylaluminumHCID 23552715HCID 23552715, compound

Product 1

HCID 69920753HCID 69920753, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 35 mg (0.44 mmol) diethylamine in 0.5 ml dioxane was added 0.5 ml methylaluminoxane (10% in toluene) (in a variant trimethylaluminium was used instead of methylaluminoxane which proofed to give comparable results) and stirred for 1 h at room temperature. 31 mg (0.11 mmol) 5-Amino-2-(5-methyl-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid methyl ester in 1 ml dioxane was added and the mixture was heated to 80° C. for 72 h. After addition of 0.4 ml 1N HCl the mixture was evaporated to dryness and the residue was taken up in 1.5 ml DMSO, filtered, and the title compound was isolated by reversed phase HPLC eluting with a water/acetonitrile gradient to yield 8.6 mg (25%).

Workup

  1. customto give comparable
  2. customresults) and
  3. temperaturethe mixture was heated to 80° C. for 72 h
  4. customwas evaporated to dryness
  5. filtrationfiltered

Sources & evidence

ORD record
ord-b211d80b113745f190a53314cdfb2162
Source dataset
uspto-grants-2003_01
Patent number
US06506772B1

Reaction notes

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