Trifluoroacetic acid → HCID 86724456, compound

HRID 2369575Notes

Reaction equation

HRID 2369575 reaction equation
[F:1][C:2]1[C:7]2[O:8][CH2:9][C:10]3[C:15]([C:6]=2[CH:5]=[CH:4][C:3]=1[OH:20])=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[N:12][CH:11]=3.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:39][C@@H:40]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:41][CH:42]([CH3:44])[CH3:43])(=O)=O>CN(C=O)C.O>[C:49]([O:48][C:46](=[O:47])[NH:45][C@@H:40]([CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:39][O:20][C:3]1[CH:4]=[CH:5][C:6]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[CH:14]=3)[CH2:9][O:8][C:7]=2[C:2]=1[F:1])([CH3:50])([CH3:52])[CH3:51]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 10379776HCID 10379776, compoundHCID 136378616HCID 136378616, compound

Product 1

HCID 86724456HCID 86724456, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of N-(7-fluoro-8-hydroxy-5H-chromeno[3,4-c]pyridin-2-yl)acetamide, TFA (70 mg, 0.170 mmol) and potassium carbonate (97 mg, 0.704 mmol) in DMF (4 mL) was added (S)-2-((tert-butoxycarbonyl)amino)-4-methylpentyl methanesulfonate (52.0 mg, 0.176 mmol) at room temperature and the reaction mixture was heated to 90° C. for 1 h. After completion of reaction, the volatiles were removed under reduced pressure to afford a brown residue. To this residue water (15 mL) was added and the solution extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water (30 mL), brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure to afford (S)-tert-butyl(1-((2-acetamido-7-fluoro-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (90 mg, 0.066 mmol, 37% yield) as a brown oil. The product was carried forward without further purification. LCMS (ESI) m/e 472.2 [(M−H)−, calcd for C25H31FN3O5 472.2]; LC/MS retention time (Method E): tR=1.99 min.

Workup

  1. customAfter completion of reaction
  2. customthe volatiles were removed under reduced pressure
  3. customto afford a brown residue
  4. extractionthe solution extracted with ethyl acetate (2×20 mL)
  5. washThe combined organic layers were washed with water (30 mL), brine (20 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5845af31031348daa998e693eaaaa8c8
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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