Trifluoroacetic acid → HCID 117728324, compound

HRID 718619Notes

Reaction equation

HRID 718619 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:40]=[CH:39][C:31]([C:32]([O:34]C(C)(C)C)=[O:33])=[CH:30][CH:29]=4)=[C:14]([CH2:16][S:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:40]=[CH:39][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=4)=[C:14]([CH2:16][S:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117732489HCID 117732489, compound

Product 1

HCID 117728324HCID 117728324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 34b (347 mg, 0.627 mmol) was placed in an 8 mL vial equipped with a stir bar and then DCM (4 mL) was added and the solid dissolved. TFA (2 mL) was added dropwise and then the reaction was stirred at rt for 4 h. The solvent was removed under reduced pressure and then the residue was dissolved in DCM (10 mL) and MeOH (3 mL) and the solvent was removed under reduced pressure. The residue was triturated with MeOH (10 mL) to afford a white precipitate that was isolated by filtration. The residual solvent was removed under reduced pressure to afford the title compound 116. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 13.05 (br. s., 1H), 8.12-8.20 (m, 2H), 8.06 (d, J=8.6 Hz, 2H), 7.89 (d, J=8.1 Hz, 3H), 7.59-7.71 (m, 2H), 7.47-7.53 (m, 1H), 7.43 (d, J=8.6 Hz, 1H), 6.40 (d, J=5.6 Hz, 1H), 4.82 (s, 2H), 3.85-3.98 (m, 4H), 3.66-3.78 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C27H23N5O3S: 498.2 (M+H). Found: 498.4.

Workup

  1. customvial equipped with a stir bar
  2. dissolutionthe solid dissolved
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (10 mL)
  5. customMeOH (3 mL) and the solvent was removed under reduced pressure
  6. customThe residue was triturated with MeOH (10 mL)
  7. customto afford a white precipitate that
  8. customwas isolated by filtration
  9. customThe residual solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8667debdb3fa4b08ad0924fa082c8bf2
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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