Trifluoroacetic acid → HCID 67220605, compound

HRID 1510829Notes

Reaction equation

HRID 1510829 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:47]=[CH:46][C:27]4[C:28]([NH:31][C:32]([C@@H:34]5[CH2:38][CH2:37][CH2:36][N:35]5C(OC(C)(C)C)=O)=[O:33])=[N:29][O:30][C:26]=4[CH:25]=3)=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C.[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49]>C(Cl)Cl>[F:51][C:50]([F:53])([F:52])[C:48]([OH:54])=[O:49].[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:47]=[CH:46][C:27]4[C:28]([NH:31][C:32]([C@@H:34]5[CH2:38][CH2:37][CH2:36][NH:35]5)=[O:33])=[N:29][O:30][C:26]=4[CH:25]=3)=[CH:22][CH:23]=2)=[CH:16][N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 49855447HCID 49855447, compound

Product 1

HCID 67220605HCID 67220605, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-tert-butyl 2-(6-(4-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)benzo[d]isoxazol-3-ylcarbamoyl)pyrrolidine-1-carboxylate (0.115 mg, 0.178 mmol) in CH2Cl2 (3 mL) was treated with TFA (1 mL) and the solution was allowed to stir at rt for 2 h. The solvents were removed in vacuo and the residue was purified by prep HPLC (CH3CN—H2O-TFA) to give the TFA salt of the title compound (74.8 mg, 53%) as a colorless glass. 1H NMR (400 MHz, DMSO-d6) δ 11.78 (s, 1H), 9.53-9.58 (m, 1H), 9.30-9.36 (m, 1H), 8.97-9.04 (m, 1H), 8.79-8.84 (m, 1H), 8.10 (d, J=8.6 Hz, 1H), 8.06 (s, 1H), 7.93 (AB doublet of AB quartet 2H), 7.86 (AB doublet of AB quartet 2H), 7.78-7.83 (m, 1H), 4.73-4.78 (m, 2H), 4.51-4.54 (m, 2H), 3.28-3.38 (m, 4H), 1.95-2.22 (m, 6H). LCMS: Anal. Calcd. for C25H26N6O2: 442; found: 443 (M+H)+.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by prep HPLC (CH3CN—H2O-TFA)

Sources & evidence

ORD record
ord-87931a865c6e486faf40f6d7e016aa89
Source dataset
uspto-grants-2012_07
Patent number
US08211928B2

Reaction notes

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