Pyrrolidone carboxylic acid → HCID 58477259, compound

HRID 876528Notes

Reaction equation

HRID 876528 reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[NH:10][CH:9]([C:11]([OH:13])=O)[CH2:8][CH2:7]1.[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[O:23][C:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]([F:34])([F:33])[F:32])=[CH:21][C:20]2=[O:35].N1C=CC=CC=1>C1COCC1.CN(C=O)C>[O:5]=[C:6]1[NH:10][CH:9]([C:11]([NH:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[O:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:32])[F:33])=[CH:21][C:20]3=[O:35])=[O:13])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 499Pyrrolidone carboxylic acidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 58477328HCID 58477328, compound

Product 1

HCID 58477259HCID 58477259, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Thionylchloride (236 mg, 2.0 mmol) was added to a solution of 5-oxopyrrolidine-2-carboxylic acid 120 (170 mg, 1.32 mmol) in THF (5 mL) at 0° C. DMF (1 drop) was added and the solution was allowed to warm to room temperature for 2 h then cooled to 0° C. A solution of 8-amino-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one 11 (100 mg, 0.33 mmol) and pyridine (0.5 mL) in THF (1 mL) was added and the reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was concentrated to dryness, dissolved in EtOAc, washed with sat. aq NaHCO3, brine, and dried (Na2SO4). The crude residue was purified by preparative TLC eluting with EtOAc to give Compound 313. MS (ESI) calcd for C21H15F3N2O4: 416.1. found: 417 [M+H].

Workup

  1. temperaturethen cooled to 0° C
  2. temperatureto warm to room temperature
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutiondissolved in EtOAc
  5. washwashed with sat. aq NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. customThe crude residue was purified by preparative TLC
  8. washeluting with EtOAc

Sources & evidence

ORD record
ord-6537d3f51e2a4868b9937490996ea6bd
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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