Trifluoroacetic acid → HCID 86693211, compound

HRID 575204Notes

Reaction equation

HRID 575204 reaction equation
[F:1][C:2]1[C:18]([C:19]#[C:20][C:21]([OH:36])([C:23]2[N:24](COCC[Si](C)(C)C)[CH:25]=[CH:26][N:27]=2)[CH3:22])=[CH:17][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([C:14]([NH2:16])=[O:15])[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:1][C:2]1[C:18]([C:19]#[C:20][C:21]([OH:36])([C:23]2[NH:27][CH:26]=[CH:25][N:24]=2)[CH3:22])=[CH:17][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([C:14]([NH2:16])=[O:15])[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 86693212HCID 86693212, compound

Product 1

HCID 86693211HCID 86693211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9-fluoro-10-(3-hydroxy-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide (200 mg, 0.39 mmol, 1.00 equiv) and TFA (1.5 mL) in dichloromethane (4.5 mL) was stirred for 5 h at room temperature. The resulting solution was diluted with 50 mL of dichloromethane. The pH value of the solution was adjusted to 9 with saturated potassium carbonate. The resulting mixture was washed with water, dried over sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (10/1) to give the titled compound as an off-white solid.

Workup

  1. washThe resulting mixture was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e6d020e047f045138f2c96b438f3dc75
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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