Trifluoroacetic acid → HCID 178509554, compound

HRID 1424159Notes

Reaction equation

HRID 1424159 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([C@@H:18]([NH:42]C(=O)OC(C)(C)C)[CH2:19][C:20](=[O:41])[NH:21]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[NH:15][C:14]=2[CH:50]=1.FC(F)(F)C(O)=O>>[NH2:42][C@H:18]([C:16]1[NH:17][C:13]2[CH:12]=[CH:11][C:10]([C:3]3[CH:4]=[CH:5][C:6]([C:8]#[N:9])=[CH:7][C:2]=3[Cl:1])=[CH:50][C:14]=2[N:15]=1)[CH2:19][C:20]([NH2:21])=[O:41]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699059HCID 86699059, compound

Product 1

HCID 178509554HCID 178509554, compoundYield 80.8%

Procedure

To (S)-tert-butyl (1-(6-(2-chloro-4-cyanophenyl)-1H-benzo[d]imidazol-2-yl)-3-oxo-3-(tritylamino)propyl)carbamate (Preparation 15, 35 mg, 0.051 mmol) was added trifluoroacetic acid (1.3 mL, 17 mmol) and the mixture stirred at room temperature for 2 hours. The reaction solution was concentrated in vacuo and azeotroped with methanol. The residue was purified using silica gel column chromatography eluting with 0-100% CMA80/methylene chloride to afford the title compound (14 mg, 65%) as a light yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customazeotroped with methanol
  3. customThe residue was purified
  4. washeluting with 0-100% CMA80/methylene chloride

Sources & evidence

ORD record
ord-1e361920ffe24d588bc2167942b5c76c
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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