Butylamine → HCID 59750472, compound

HRID 748327Notes

Reaction equation

HRID 748327 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.[CH2:21]([NH2:25])[CH2:22][CH2:23][CH3:24]>O1CCCC1>[CH2:21]([NH:25][C:12]([C:10]1[CH:9]=[CH:8][C:7]2[C:2](=[O:1])[N:3]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[S:5][C:6]=2[CH:11]=1)=[O:14])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 22939340HCID 22939340, compound

Product 1

HCID 59750472HCID 59750472, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N,N′-carbonyldiimidazole (570 mg, 3.5 mmol) was added to a mixture of 4-oxo-2-(2-pyridyl)-4H-1,3-benzothiazine-7-carboxylic acid (800 mg, 2.8 mmol) and tetrahydrofuran (20 ml), and the mixture was stirred at 60° C. for 2 hrs. Successively, butylamine (410 mg, 5.6 mmol) was added to the reaction mixture, and the mixture was stirred at 60° C. for 30 minutes. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (1:3, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (478 mg, 50%) as white crystals.

Workup

  1. stirringthe mixture was stirred at 60° C. for 30 minutes
  2. customThe solvent was evaporated
  3. washThe fractions eluted with hexane-ethyl acetate (1:3
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-068c9d14baa244609350553040e82cc4
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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