Trifluoroacetic acid → (S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-6,6-dimethyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxamide

HRID 75122Notes

Reaction equation

HRID 75122 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH2:14][C:15]([CH3:27])([CH3:26])[CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][C:12]3=[C:11]([C:28](=[O:39])[NH:29][C@@H:30]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:31]([NH:33][CH3:34])=[O:32])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH2:14][C:15]([CH3:27])([CH3:26])[CH2:16][NH:17][CH2:18][C:12]3=[C:11]([C:28]([NH:29][C@@H:30]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:31]([NH:33][CH3:34])=[O:32])=[O:39])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66660532HCID 66660532, compound

Product 1

HCID 66660428(S)-3-(3,4-difluorophenyl)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-6,6-dimethyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step 1 above (128 mg, 0.23 mmol) was dissolved in 2 mL of DCM and carefully treated with 2 mL of TFA. The mixture was stirred for 45 minutes and concentrated in vacuo. The residue was suspended in 5 mL of toluene and concentrated in vacuo. The residue was dried in a vacuum oven overnight to give the title compound (182 mg, 99%) as a poly-TFA salt. LCMS (+ESI) m/z: 448.3 [MH]+1

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationconcentrated in vacuo
  3. customThe residue was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-88be2eef04a2467185578bdcf79f622a
Source dataset
uspto-grants-2014_09
Patent number
US08835422B2

Reaction notes

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