Trifluoroacetic acid → HCID 178509553, compound

HRID 1424158Notes

Reaction equation

HRID 1424158 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:32]1[NH:36][C:35]2[CH:37]=[CH:38][C:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[C:43]([F:49])[CH:42]=3)=[CH:40][C:34]=2[N:33]=1)[CH2:9][C:10](=[O:31])[NH:11]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][C@H:8]([C:32]1[NH:36][C:35]2[CH:37]=[CH:38][C:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[C:43]([F:49])[CH:42]=3)=[CH:40][C:34]=2[N:33]=1)[CH2:9][C:10]([NH2:11])=[O:31]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454216HCID 178454216, compound

Product 1

HCID 178509553HCID 178509553, compoundYield 66.3%

Procedure

(S)-tert-butyl(1-(5-(4-cyano-3-fluorophenyl)-1H-benzo[d]imidazol-2-yl)-3-oxo-3-(tritylamino)propyl)carbamate (Preparation 17, 28 mg, 0.042 mmol) was dissolved in trifluoroacetic acid (1.1 mL, 14 mmol) and stirred for 2.5 hours. The reaction mixture was concentrated in vacuo, azeotroped with methanol (3×), and purified by silica gel column chromatography eluting with 0-100% CMA80/methylene chloride to afford the title compound (9 mg, 37%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customazeotroped with methanol (3×)
  3. custompurified by silica gel column chromatography
  4. washeluting with 0-100% CMA80/methylene chloride

Sources & evidence

ORD record
ord-ddb9fd82344545c9b19338ee666bae09
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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