Trifluoroacetic acid → HCID 178463306, compound

HRID 2122016Notes

Reaction equation

HRID 2122016 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][C:22]([NH:24][C:25]([NH:34]C(OC(C)(C)C)=O)=[N:26]C(OC(C)(C)C)=O)=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:42][C:43]1[CH:48]=[C:47]([C:49]#[N:50])[CH:46]=[CH:45][C:44]=1[NH:51][CH2:52][CH3:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][C:22]([NH:24][C:25]([NH2:34])=[NH:26])=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:42][C:43]1[CH:48]=[C:47]([C:49]#[N:50])[CH:46]=[CH:45][C:44]=1[NH:51][CH2:52][CH3:53])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178463305HCID 178463305, compound

Product 1

HCID 178463306HCID 178463306, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the product of Example 273 (116 mg, 0.15 mmol) in anhydrous DCM (6 mL) was added TFA (3 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, then at ambient temperature for 14 h. The solvent was removed in vacuo, and the residue was purified by reverse-phase HPLC (C18 column), eluting with 0.05% TFA in MeCN—H2O (1:9 to 9:1) to afford the title compound (25 mg, 30%) as a yellow solid. 1H-NMR (DMSO-d6): δ 9.65 (1H, s), 7.72 (1H, d), 7.48 (1H, d), 7.41-7.25 (8H, m), 7.15 (1H, d), 6.65 (1H, d), 5.14 (2H, s), 3.84 (3H, s), 3.07 (2H, m), 1.01 (3H, t); MS(ESI): 555 (MH+).

Workup

  1. waitat ambient temperature for 14 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by reverse-phase HPLC (C18 column)
  4. washeluting with 0.05% TFA in MeCN—H2O (1:9 to 9:1)

Sources & evidence

ORD record
ord-15feb37c6c3b454ba19c21b53de4d3be
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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