Trifluoroacetic acid → HCID 10008274, compound

HRID 2102244Notes

Reaction equation

HRID 2102244 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:31]=[CH:30][C:17]([C:18]([NH:20][CH2:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:19])=[CH:16][CH:15]=3)[N:11]=[C:10]([C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[CH:33]=3)[CH:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([NH:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:19])=[CH:30][CH:31]=3)[N:11]=[C:10]([C:32]3[CH:33]=[C:34]([Cl:39])[CH:35]=[C:36]([Cl:38])[CH:37]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68621753HCID 68621753, compound

Product 1

HCID 10008274HCID 10008274, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from step F (30 mg, 0.047 mmol) in DCM (2 mL) was added trifluroacetic acid (2 mL). The reaction was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and lyophilized from acetonitrile-water to give the title compound. 1H NMR (DMSO, 500 MHz): δ 8.49(t, J=5.5 Hz, 1H), 7.89 (d, J=1.8 Hz, 2H), 7.75 (d, J=8.2 Hz, 2H), 7.7 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.22 (s, 1H), 7.11 (d, J=8.2 Hz, 2H), 5.5 (s, 2H), 3.45 (q, J=7.1 Hz, 2H), 2.49 (t, J=6.8 Hz, 2H). LC-MS: 2.59 min; (M+H)=571.9.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3471331a9820414cbd126acb1b646aec
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

Loading…