Trifluoroacetic acid → 5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester trifluoroacetate

HRID 1253904Notes

Reaction equation

HRID 1253904 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:15]=1[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][C:11]1[CH:23]=[CH:24][CH:25]=[CH:26][C:10]2=1)=[O:5])[CH3:2].[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]>C(Cl)Cl>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:15]=1[CH2:14][NH:13][CH2:12][C:11]1[CH:23]=[CH:24][CH:25]=[CH:26][C:10]2=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 687775784H,6H-2,5,10b-triaza-benzo[e]azulene-3,5-dicarboxylic acid 5-tert-butyl ester 3-ethyl ester

Product 1

HCID 687776935,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester trifluoroacetateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4H,6H-2,5,10b-Triaza-benzo[e]azulene-3,5-dicarboxylic acid 5-tert-butyl ester 3-ethyl ester (300 mg, 1.14 mmol) in DCM (30 mL), was added trifluoroacetic acid (3.42 mL, 3 ml/mmol) and the reaction mixture was stirred for 2 h. After the completion of the reaction as confirmed by TLC, excess of trifluoroacetic acid and DCM were removed in vacuo to afford 5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester trifluoroacetate (295 mg, 93%) as a gummy solid which was used without any further purification for the next step.

Workup

  1. customAfter the completion of the reaction
  2. customwere removed in vacuo

Sources & evidence

ORD record
ord-072dcd9d50c04c60813d6be067130341
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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