Pyrrolidine → HCID 59750447, compound

HRID 748328Notes

Reaction equation

HRID 748328 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([OH:14])=O)=[CH:11][C:6]=2[S:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:3]1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>O1CCCC1>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:4]1[S:5][C:6]2[CH:11]=[C:10]([C:12]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:14])[CH:9]=[CH:8][C:7]=2[C:2](=[O:1])[N:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 22939340HCID 22939340, compound

Product 1

HCID 59750447HCID 59750447, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N,N′-carbonyldiimidazole (445 mg, 2.7 mmol) was added to a mixture of 4-oxo-2-(2-pyridyl)-4H-1,3-benzothiazine-7-carboxylic acid (600 mg, 2.1 mmol) and tetrahydrofuran (20 ml), and the mixture was stirred at 60° C. for 2 hrs. Successively, pyrrolidine (300 mg, 4.2 mmol) was added to the reaction mixture, and the mixture was stirred at 60° C. for 1 hr. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (83 mg, 11%) as white crystals.

Workup

  1. stirringthe mixture was stirred at 60° C. for 1 hr
  2. customThe solvent was evaporated
  3. washThe fractions eluted with ethyl acetate
  4. customwere collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-d00616aa95f0410dbb2985a45326ac96
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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