Trifluoroacetic acid → 2-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetic acid

HRID 1485402Notes

Reaction equation

HRID 1485402 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH:13]([CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[C:12]3=[N:24][N:25]=[C:26]([CH3:27])[N:11]3[C:10]3[CH:28]=[CH:29][CH:30]=[CH:31][C:9]2=3)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH:13]([CH2:16][C:17]([OH:19])=[O:18])[C:12]3=[N:24][N:25]=[C:26]([CH3:27])[N:11]3[C:10]3[CH:28]=[CH:29][CH:30]=[CH:31][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70979588tert-butyl 2-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetate

Product 1

HCID 709789952-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetate (90 mg, 0.21 mmol) in 5 mL of DCM, was added TFA (1 mL). The mixture was stirred at room temperature for 2 h. The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with DCM:MeOH=20:1 to give 2-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetic acid as a yellow solid (68 mg, 87%). LRMS (M+H)+: 382 m/z.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography
  3. washeluting with DCM

Sources & evidence

ORD record
ord-d1200a1387894df485e502acf34ac6f8
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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