Acetic Anhydride → HCID 57843254, compound

HRID 734961Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=2)=[CH:13][CH:12]=3)[CH2:4][CH2:3]1.S(Cl)(Cl)(=O)=O.[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1.O.C(=O)(O)[O-].[Na+]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:30](=[O:32])[CH3:31])=[N:22][CH:23]=2)=[CH:13][CH:12]=3)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 5-[3-(4-methyl-1-piperazinyl)-6-quinoxalinyl]-2-pyridinamine (0.46 mmol) in pyridine (3 ml) was treated with a sulfonyl chloride, acyl chloride or anhydride such as acetic anhydride (0.56 mmol) and heated at 50° C. for 18 hour. The reaction mixture was treated with another portion of acetic anhydride (0.10 mmol) and stirred for another 2 days. The reaction mixture was diluted with water and saturated sodium bicarbonate (aq) and extracted with ethyl acetate. The ethyl acetate layer was dried over Na2SO4 filtered and concentrated under reduced pressure. The residue was taken into hot ethyl acetate and diluted with hexanes and cool to 0° C. The reaction mixture was filtered and washed with hexanes to give the title compound (98 mg, 58%). MS(ES)+ m/e 321 [M+H]+.

Workup

extractionextracted with ethyl acetate
dry with materialThe ethyl acetate layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
additiondiluted with hexanes
temperaturecool to 0° C
filtrationThe reaction mixture was filtered
washwashed with hexanes

Sources & evidence

ORD record: ord-e2f2bf9bb78249848843f1db36264fb6
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592342B2

Reaction notes

Loading…