Trifluoroacetic acid → HCID 66995313, compound

HRID 449296Notes

Reaction equation

HRID 449296 reaction equation
[Cl:1][C:2]1[C:35]([F:36])=[CH:34][CH:33]=[C:32]([F:37])[C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]3[CH:15]=[N:16][N:17]([CH:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)[CH:18]=3)=[CH:12][CH:13]=[C:8]2[N:7]=[N:6]1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>ClCCl>[ClH:1].[Cl:1][C:2]1[C:35]([F:36])=[CH:34][CH:33]=[C:32]([F:37])[C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]3[CH:15]=[N:16][N:17]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH:18]=3)=[CH:12][CH:13]=[C:8]2[N:7]=[N:6]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 58514886HCID 58514886, compound

Product 1

HCID 66995313HCID 66995313, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 166 (0.240 g, 0.453 mmol) in dichloromethane (3 ml) cooled to 0° C., TFA (0.1 ml) was added and warmed to RT. After 2 h, the reaction mixture was poured in ice water and pH was adjusted to call with 10% NaOH solution and extracted with ethyl acetate, washed with brine, dried over sodium sulphate and concentrated. The residue was dissolved in THF (1 ml), ether saturated with HCl (1 ml) was added at 0° C. and stirred for 15 min. The precipitate formed was filtered and washed with ether and dried under vacuum to afford the title compound as an off-white solid (0.090 g, 43%). M.P.: 85-87° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.48 (d, J=1.5 Hz, 1H), 8.45 (s, 1H), 8.09 (s, 1H), 7.79 (d, J=8.7 Hz, 1H), 7.60 (dt, J=13.8, 4.8 Hz, 1H), 7.45 (dt, J=13.4, 4.2 Hz, 1H), 6.01 (s, 2H), 4.29 (m, 1H), 3.07 (d, J=12.4 Hz, 2H), 2.63 (m, 2H), 1.98 (m, 2H), 1.85 (m, 2H). MS (m/z):: 429.69 (M+-HCl).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in THF (1 ml)
  6. additionether saturated with HCl (1 ml) was added at 0° C.
  7. customThe precipitate formed
  8. filtrationwas filtered
  9. washwashed with ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-ed0e8ad48675482e8cc17650915baf54
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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