Trifluoroacetic acid → [4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid

HRID 900141Notes

Reaction equation

HRID 900141 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][N:8]1[C:17](=[O:18])[CH:16]([CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[C:15]2[N:11]([C:12]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:13][N:14]=2)[C:10]2[CH:35]=[CH:36][CH:37]=[CH:38][C:9]1=2)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([CH2:19][CH:16]2[C:15]3[N:11]([C:12]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:13][N:14]=3)[C:10]3[CH:35]=[CH:36][CH:37]=[CH:38][C:9]=3[N:8]([CH2:7][C:6]([OH:39])=[O:5])[C:17]2=[O:18])=[CH:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69312483[4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid tert-butyl ester

Product 1

HCID 68607281[4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acidYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid tert-butyl ester (4.26 g, 8.19 mmol) in CH2Cl2 (27 mL) was added TFA (9.5 mL, 0.123 mmol). The reaction was stirred at room temperature for 8 hours and was concentrated in vacuo. The residue was dissolved in CH2Cl2 (50 mL) and Et2O (15 mL) and was stirred for 24 hours. The precipitate was filtered and was washed with Et2O to provide 2.33 g of [4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid. 1H NMR (DMSO-d6) δ 10.79 (s, 1H), 7.70 (d, 1H), 7.54-7.38 (m, 7H), 7.26 (d, 1H), 7.17 (m, 2H), 6.98 (t, 1H), 6.88 (m, 2H), 4.90 (d, 1H), 4.49 (d, 1H), 3.82 (t, 1H), 3.59 (m, 2H).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  3. stirringEt2O (15 mL) and was stirred for 24 hours
  4. filtrationThe precipitate was filtered
  5. washwas washed with Et2O

Sources & evidence

ORD record
ord-e3d37638bafe4a39958b1dacd39ab3d4
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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