Trifluoroacetic acid → (E)-3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-acrylic Acid

HRID 220866Notes

Reaction equation

HRID 220866 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:40])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([C:22]([N:24]2[CH2:33][C:32]3[CH:31]=[N:30][N:29]([CH3:34])[C:28]=3[NH:27][C:26]3[CH:35]=[CH:36][CH:37]=[CH:38][C:25]2=3)=[O:23])=[CH:18][C:17]=1[CH3:39])(C)(C)C>ClCCl>[CH3:39][C:17]1[CH:18]=[C:19]([C:22]([N:24]2[CH2:33][C:32]3[CH:31]=[N:30][N:29]([CH3:34])[C:28]=3[NH:27][C:26]3[CH:35]=[CH:36][CH:37]=[CH:38][C:25]2=3)=[O:23])[CH:20]=[CH:21][C:16]=1/[CH:15]=[CH:14]/[C:13]([OH:40])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136128393(E)-3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-acrylic Acid Tert-butyl Ester

Product 1

HCID 136128358(E)-3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-acrylic AcidYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to a solution of (E)-3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-acrylic acid tert-butyl ester from Example E45.2 (338 mg, 0.76 mmol) in dichloromethane (10 ml) and the mixture was stirred for 45 min at room temperature. Solvents were removed in vacuo and azeotroped with dichloromethane to yield the title compound (337 mg, 80%).

Workup

  1. customSolvents were removed in vacuo
  2. customazeotroped with dichloromethane

Sources & evidence

ORD record
ord-79864fbfd55e4efba0a4bb7361c80d15
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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