Trifluoroacetic acid → HCID 178437985, compound

HRID 1404807Notes

Reaction equation

HRID 1404807 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:17]=[C:16]4[N:18]([CH2:21][C:22]5[CH:23]=[C:24]6[C:29](=[CH:30][CH:31]=5)[N:28]=[CH:27][CH:26]=[CH:25]6)[N:19]=[N:20][C:15]4=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[N:5](C(OC(C)(C)C)=O)[N:4]=1)[CH3:2].C(O)(C(F)(F)F)=O.[OH-].[Na+]>ClCCl>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:17]=[C:16]4[N:18]([CH2:21][C:22]5[CH:23]=[C:24]6[C:29](=[CH:30][CH:31]=5)[N:28]=[CH:27][CH:26]=[CH:25]6)[N:19]=[N:20][C:15]4=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[NH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 58514851HCID 58514851, compound

Product 1

HCID 178437985HCID 178437985, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 181 (0.050 g, 0.099 mmol) in dichloromethane (1 ml) cooled to 0° C., TFA (0.5 ml) was added and warmed to RT. After 2 h, the reaction mixture was poured in ice water and pH was adjusted to ca. 11 with 10% NaOH solution and extracted with ethyl acetate, washed with brine, dried over sodium sulphate and concentrated to afford the title compound as a yellow solid (0.023 g, 61%). M.P.: 211-213° C. MS (m/z): 406.08 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae10ef54f8034f8685164e8d369c2665
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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