Trifluoroacetic acid → 945529-91-9

HRID 1944068Notes

Reaction equation

HRID 1944068 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[CH2:12][N:11]([C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[S:17][C:16]=2[NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])=[O:14])[CH2:10]1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O>[NH2:7][CH2:8][CH:9]1[CH2:10][N:11]([C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[S:17][C:16]=2[NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])=[O:14])[CH2:12]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 68918287HCID 68918287, compound

Product 1

HCID 68915728945529-91-9

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 28 (65 mg, 0.11 mmol) in DCM (7 mL) was treated with trifluoroacetic acid (3 mL) and stirred for 1 h at r.t. The reaction mixture was concentrated in vacuo to give a yellow gum, which was dissolved in water (25 mL) and basified to pH 10 with sodium carbonate. The aqueous solution was extracted with 5% methanol in DCM (4×25 mL), and the extracts combined, then dried (Na2SO4), filtered and concentrated in vacuo. The crude product was subjected to column chromatography (SiO2, 4:1 DCM/methanol) to give the title compound as a gummy solid, which was triturated from ether to give a cream-coloured powder (34 mg, 63%). δH (DMSO-d6) 8.31 (1H, m), 7.93 (1H, m), 7.72 (1H, dd, J 1.5, 10.5 Hz), 7.55 (1H, m), 7.37 (1H, dd, J 4.6, 8.1 Hz), 7.29-7.24 (1H, m), 4.88 (2H, br s), 4.03-3.97 (2H, m), 3.71-3.67 (2H, m), 2.65 (1H, m), 2.70-2.68 (2H, m). LCMS RT 2.93 minutes, (ES−) 481 (M−H)−, (ES+) 483 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a yellow gum, which
  3. extractionThe aqueous solution was extracted with 5% methanol in DCM (4×25 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e683baaf34594e4bbd5a4eeca7d402b9
Source dataset
uspto-grants-2013_03
Patent number
US08394822B2

Reaction notes

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