Trifluoroacetic acid → HCID 17755955, compound

HRID 1723993Notes

Reaction equation

HRID 1723993 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:17][CH:16]=1.[F-].[K+].C(O)(C(F)(F)[F:41])=O>C(#N)C.O>[F:41][CH2:24][CH2:23][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][NH:13][C:3]2[O:4][C:5]3[C:10]([C:11](=[O:12])[C:2]=2[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 522689Potassium FluorideHCID 17755954HCID 17755954, compound

Product 1

HCID 17755955HCID 17755955, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of toluene-4-sulfonic acid 4-{4-[(3-methyl-4-oxo-4H-chromen-2-ylamino)-methyl]-phenyl}-butyl ester (24 mg, 0.049 mmol) in ACN (1.1 mL) was added K222 (37 mg, 0.098 mmol) followed by KF (6 mg, 0.098 mmol). The reaction stirred in a 90° C. oil bath for 30 minutes under nitrogen atmosphere, monitored by LC-MS. The reaction was then cooled to room temperature and injected directly onto the preparative HPLC coloum chromatography (Luna, 10u, C18, 250×21.2 mm 10 micro, 60% of water in 90% acetonitrile in water with 0.1% TFA as the modifier in both mobile phases). The desired fractions were collected and neutralized to pH 7.6, then lyophilized. The material was re-purified by flash column chromatography (3:1 Hexane:ethyl acetate) to obtain the desired product as a solid (0.3 mg, <2% yield).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customThe desired fractions were collected
  3. customThe material was re-purified by flash column chromatography (3:1 Hexane:ethyl acetate)

Sources & evidence

ORD record
ord-5f1d154b442b4aeb8c9b64aa772f5b4e
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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