Trifluoroacetic acid → HCID 49855448, compound

HRID 1510831Notes

Reaction equation

HRID 1510831 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:25]=[CH:26][C:27]4[O:31][N:30]=[C:29]([NH:32][C:33]([C@@H:35]5[CH2:39][CH2:38][CH2:37][N:36]5C(OC(C)(C)C)=O)=[O:34])[C:28]=4[CH:47]=3)=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[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:25]=[CH:26][C:27]4[O:31][N:30]=[C:29]([NH:32][C:33]([C@@H:35]5[CH2:39][CH2:38][CH2:37][NH:36]5)=[O:34])[C:28]=4[CH:47]=3)=[CH:22][CH:23]=2)=[CH:16][N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67220647HCID 67220647, compound

Product 1

HCID 49855448HCID 49855448, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 2-(5-(4-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)benzo[d]isoxazol-3-ylcarbamoyl)pyrrolidine-1-carboxylate (TFA salt 400 mg, 0.622 mmol) in DCM (5 mL) was added TFA (2 ml, 26.0 mmol) and the reaction mixture was stirred for 3 h at room temp. The solvents were removed in vacuo and the residue was taken up in 10% Methanol/CH2Cl2 and filtered through an MCX cartridge (Strata XC). The cartridge was washed with methanol and the compound was eluted with a solution of NH3 in methanol (2M). The appropriate fractions were concentrated in vacuo to afford the title compound (248 mg, 0.560 mmol, 90% yield) as yellow solid. 1H NMR (500 MHz, CD3OD) δ 8.31 (s, 1H), 7.93 (dd, J=1.8, 8.9 Hz, 1H), 7.83 (app d, J=8.5 Hz, 2H), 7.68 (app d, J=8.5 Hz, 2H), 7.65 (d, J=8.5 Hz, 1H), 7.50 (s, 1H), 4.74 (t, J=7.9 Hz, 1H), 4.37 (s, br, 1H), 3.42-3.47 (m, 1H), 3.32-3.38 (m, 2H), 3.22-3.27 (m, 1H), 2.43-2.51 (m, 2H), 2.30-2.37 (m, 1H), 2.20-2.27 (m, 1H), 2.09-2.18 (m, 2H), 1.98-2.05 (m, 1H). LCMS: Anal. Calcd. for C25H26N6O2: 442; found: 443 (M+H)+.

Workup

  1. customThe solvents were removed in vacuo
  2. filtrationfiltered through an MCX cartridge (Strata XC)
  3. washThe cartridge was washed with methanol
  4. washthe compound was eluted with a solution of NH3 in methanol (2M)
  5. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-f911a066855a4314a9f954297aa08698
Source dataset
uspto-grants-2012_07
Patent number
US08211928B2

Reaction notes

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