Methanol → HCID 68775975, compound

HRID 1253890Notes

Reaction equation

HRID 1253890 reaction equation
C(OC([N:8]1[CH2:17][C:16]2[N:12]([CH:13]=[N:14][N:15]=2)[C:11]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:10]=2[CH2:9]1)=O)(C)(C)C.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].CO>C(Cl)Cl>[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[F:22][C:19]1[CH:20]=[CH:21][C:10]2[CH2:9][NH:8][CH2:17][C:16]3[N:12]([CH:13]=[N:14][N:15]=3)[C:11]=2[CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 68777580HCID 68777580, compound

Product 1

HCID 68775975HCID 68775975, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-fluoro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester, (1.45 g, 4.76 mmol) in dry DCM (15 mL) was added trifluoroacetic acid (14.30 mL, 3 mL/mmol) at 0° C. The reaction mixture was stirred at r.t. for 2 h under argon. After completion of the reaction as confirmed by TLC, MeOH (2×10 mL) was added and the reaction mixture was evaporated under vacuo to remove excess of solvent and trifluoroacetic acid. The remaining solvents were removed under vacuo and 9-fluoro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene trifluoroacetate (1.50 g, 4.71 mmol, 99%) was obtained as thick brown jelly. The crude compound was used as such without any further purification for the next step.

Workup

  1. customAfter completion of the reaction
  2. additionwas added
  3. customthe reaction mixture was evaporated under vacuo
  4. customto remove excess of solvent and trifluoroacetic acid
  5. customThe remaining solvents were removed under vacuo

Sources & evidence

ORD record
ord-aa026b2ef0d34f429cc0b80a80a134ae
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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