Trifluoroacetic acid → HCID 11570373, compound

HRID 1865421Notes

Reaction equation

HRID 1865421 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[N:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:11]([C@H:24]([C:26]3[CH:43]=[CH:42][C:29]([C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])=[O:31])=[CH:28][CH:27]=3)[CH3:25])[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[N:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:11]([C@H:24]([C:26]3[CH:27]=[CH:28][C:29]([C:30]([NH:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[O:31])=[CH:42][CH:43]=3)[CH3:25])[N:10]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68573051HCID 68573051, compound

Product 1

HCID 11570373HCID 11570373, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from step F (128 mg) in CH2Cl2(2 mL) was added TFA (2 mL). After the reaction was stirred at room temperature for 30 minutes, it was concentrated in vacuo and azeotroped with toluene (3×). The resulting light yellow solid was dissolved in 1,4-dioxane and lyophilized overnight to afford the title compound as a white solid. 1H NMR (CD3OD, 500 MHz) 8.82 (d, J=1.8 Hz, 1H), 8.42 (s, 1H), 8.12 (d, J=8.5 Hz, 1H), 7.99 (d, J=8.0 Hz, 1H), 7.93 (t, J=7.3 Hz, 1H), 7.90 (d, J=1.6 Hz, 2H), 7.77 (t, J=7.5 Hz, 2H), 7.71 (d, J=8.3 Hz, 2H), 7.4 (s, 1H), 7.24 (d, J=8.3 Hz, 2H), 7.06 (s, 1H), 5.71 (q, J=6.8 Hz, 1H), 3.66 (t, J=6.9 Hz, 2H), 2.63 (t, J=7.1 Hz, 2H), 2.01 (d, J=6.8 Hz, 3H). LC-MS: 3.68 min; (M+H)=559.1.

Workup

  1. concentrationit was concentrated in vacuo
  2. customazeotroped with toluene (3×)
  3. dissolutionThe resulting light yellow solid was dissolved in 1,4-dioxane
  4. waitlyophilized overnight

Sources & evidence

ORD record
ord-318b5b8ad21f40988578f5f98e5fdc3c
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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