Trifluoroacetic acid → Trifluoroacetic acid

HRID 1518383Notes

Reaction equation

HRID 1518383 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31]C(C)(C)C)=[O:30])[C:26]([CH2:36][CH2:37][CH2:38][O:39][C:40]3[CH:45]=[CH:44][C:43]([N:46]4[C:50]5=[N:51][CH:52]=[N:53][C:54]([NH:55][CH2:56][CH2:57][CH2:58][N:59]([CH3:61])[CH3:60])=[C:49]5[CH:48]=[N:47]4)=[CH:42][CH:41]=3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].C([SiH](CC)CC)C.[C:69]([OH:75])([C:71]([F:74])([F:73])[F:72])=[O:70]>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([OH:31])=[O:30])[C:26]([CH2:36][CH2:37][CH2:38][O:39][C:40]3[CH:45]=[CH:44][C:43]([N:46]4[C:50]5=[N:51][CH:52]=[N:53][C:54]([NH:55][CH2:56][CH2:57][CH2:58][N:59]([CH3:61])[CH3:60])=[C:49]5[CH:48]=[N:47]4)=[CH:42][CH:41]=3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].[C:69]([OH:75])([C:71]([F:74])([F:73])[F:72])=[O:70]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59447521HCID 59447521, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 59447537HCID 59447537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 92A (90 mg, 0.107 mmol) and triethylsilane (37.4 mg, 0.322 mmol) in DCM (1 ml) was treated with TFA (3 ml, 38.9 mmol) for 4 h. The mixture was concentrated and the residue was purified by reverse phase HPLC (mobile phase: 0%-60% acetonitrile in 0.1% TFA aqueous solution during 70 min) to provide the title compound as a TFA salt: 1H NMR (400 MHz, DMSO-D6) δ ppm 12.82 (1H, s), 9.37 (1H, s), 8.55 (1H, t) 8.34 (1H, d), 8.03 (1H, d), 7.96-8.01 (2H, m), 7.79 (1H, d), 7.55-7.63 (2H, m), 7.44-7.50 (2H, m), 7.39-7.43 (1H, m), 7.35 (2H, t), 7.05-7.09 (2H, m), 6.97 (1H, d), 4.93 (2H, s), 3.99 (2H, q), 3.87 (2H, t), 3.43-3.70 (2H, m), 3.12-3.18 (2H, m), 2.99 (2H, t), 2.82-2.87 (2H, m), 2.80 (6H, s), 1.91-2.05 (4 FI, m). LCMS (APCI) 783 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC (mobile phase: 0%-60% acetonitrile in 0.1% TFA aqueous solution during 70 min)

Sources & evidence

ORD record
ord-2e612b1da6ad4d9b92012a5a961faec2
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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