Trifluoroacetic acid → HCID 57975539, compound

HRID 1865428Notes

Reaction equation

HRID 1865428 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]=[C:19]([O:24][CH3:25])[CH:18]=4)[N:11]([C@H:26]([C:28]3[CH:45]=[CH:44][C:31]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])=[O:33])=[CH:30][CH:29]=3)[CH3:27])[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]=[C:19]([O:24][CH3:25])[CH:18]=4)[N:11]([C@H:26]([C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[CH:44][CH:45]=3)[CH3:27])[N:10]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69019343HCID 69019343, compound

Product 1

HCID 57975539HCID 57975539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from step I (64 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 product as a white solid. 1H NMR (DMSO, 500 MHz) 8.8 (d, J=1.6 Hz, 1H), 8.45 (t, J=5.5 Hz, 1H), 8.38 (s, 1H), 7.94 (s, 2H), 7.92 (d, J=8.4 Hz, 2H), 7.72 (d, J=8.0 Hz, 2H), 7.58 (s, 1H), 7.45 (d, J=2.1 Hz, 1H), 7.37 (dd, J=2.3, 8.7 Hz, 1H), 7.28 (s, 1H), 7.2 (d, J=8.0 Hz, 2H), 5.8 (q, J=6.9 Hz, 1H), 3.95 (s, 3H), 3.41 (q, J=6.9 Hz, 2H), 2.45 (t, J=7.1 Hz, 2H), 1.93 (d, J=6.9 Hz, 3H). LC-MS: 3.53 min; (M+H)=588.9.

Workup

  1. concentrationwas 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-ef10dd2f76cf4cf7a66bb5ec61335bca
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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