Cyclopropylamine → HCID 59750153, compound

HRID 748329Notes

Reaction equation

HRID 748329 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.[CH:21]1([NH2:24])[CH2:23][CH2:22]1>O1CCCC1>[CH:21]1([NH:24][C:12]([C:10]2[CH:9]=[CH:8][C:7]3[C:2](=[O:1])[N:3]=[C:4]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[S:5][C:6]=3[CH:11]=2)=[O:14])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 22939340HCID 22939340, compound

Product 1

HCID 59750153HCID 59750153, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N,N′-carbonyldiimidazole (520 mg, 3.2 mmol) was added to a mixture of 4-oxo-2-(2-pyridyl)-4H-1,3-benzothiazine-7-carboxylic acid (700 mg, 2.4 mmol) and tetrahydrofuran (20 ml), and the mixture was stirred at 60° C. for 2 hrs. Successively, cyclopropylamine (700 mg, 12.2 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 diisopropyl ether-methanol to give the titled compound (45 mg, 5%) as pale yellow 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 diisopropyl ether-methanol

Sources & evidence

ORD record
ord-c9ab19b9ef194fbab311553d0b0298d4
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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