Trifluoroacetic acid → HCID 69218834, compound

HRID 272695Notes

Reaction equation

HRID 272695 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:19]2[CH:20]=[CH:21][C:22]3[C:28](=[O:29])[NH:27][C:26]4[CH:30]=[C:31]([CH2:34][C:35]([N:37]5[CH2:41][CH2:40][CH:39]([NH:42]C(=O)OC(C)(C)C)[CH2:38]5)=[O:36])[CH:32]=[CH:33][C:25]=4[NH:24][C:23]=3[CH:50]=2)[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17]>C(Cl)Cl>[NH2:42][CH:39]1[CH2:40][CH2:41][N:37]([C:35](=[O:36])[CH2:34][C:31]2[CH:32]=[CH:33][C:25]3[NH:24][C:23]4[CH:50]=[C:19]([C:12]5[CH:13]=[CH:14][C:15]([N+:16]([O-:18])=[O:17])=[C:10]([O:9][CH3:8])[CH:11]=5)[CH:20]=[CH:21][C:22]=4[C:28](=[O:29])[NH:27][C:26]=3[CH:30]=2)[CH2:38]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69217057HCID 69217057, compound

Product 1

HCID 69218834HCID 69218834, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of Example 365 (35 mg, 0.06 mmol) in CH2Cl2 (3 mL) and stirred at room temperature for 5 hours. Concentrated under vacuum. Residue was purified by preparative HPLC to provide 25 mg (70%) of the desired product as the trifluoroacetate salt. MS (DCI) m/e 488 (M+H)+, 1H NMR (500 MHz, DMSO-d6): □ 9.87 (s, 1H), 7.99-8.08 (m, 4H), 7.95 (s, 1H), 7.80 (d, J=8.42 Hz, 1H), 7.52 (s, 1H), 7.36 (s, 1H), 7.34 (dd, J=8.42, 1.56 Hz, 1H), 7.30 (dd, J=8.11, 1.25 Hz, 1H), 6.82-6.97 (m, 2H), 4.03 (s, 3H), 3.83 (m, 1H), 3.64-3.74 (m, 2H), 3.38-3.57 (m, 4H), 2.19 (m, 1H), 1.95 (m, 1H).

Workup

  1. concentrationConcentrated under vacuum
  2. customResidue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2c736c7efe754d78901b02169ceec241
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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