Acetic Anhydride → N-[5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-acetamide

HRID 2053439Notes

Reaction equation

HRID 2053439 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:24])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:13]([Cl:23])=[CH:12][CH:11]=3)[O:4][N:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].N1C(C)=CC=CC=1C>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:23][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:24])[C:7]([C:5]1[O:4][N:3]=[C:2]([NH:1][C:25](=[O:27])[CH3:26])[CH:6]=1)=[C:16]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 79372,6-LutidineHCID 1355311763-(3-Amino-isoxazol-5-yl)-6-chloro-4-phenyl-1H-quinolin-2-one

Product 1

HCID 135495140N-[5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A flask charged with 3-(3-amino-isoxazol-5-yl)-6-chloro-4-phenyl-1H-quinolin-2-one (example 59)(22 mg, 0.063 mmol), acetic anhydride (9 mg, 0.082 mmol), 2,6-lutidine (11 mg, 0.10 mmol), DMAP (10 mg, 0.082 mmol) and DMF (0.5 mL) was heated at 50° C. for 2 hrs. The reaction was concentrated and the title compound was purified by RP-HPLC, eluting with 40-100% CH3CN in 0.1% TFA/H2O over 30 mins to give 15 mg (60%) the title cpd. 1H NMR (400 MHz, DMSO-d6) δ 12.54 (s, 1H), 10.80 (s, 1H), 7.68 (m, 1H), 7.46 (m, 4H), 7.30 (m, 2H), 6.96 (m, 2H), 2.04 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C20H14ClN3O3 379.1, found 380.0 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe title compound was purified by RP-HPLC
  3. washeluting with 40-100% CH3CN in 0.1% TFA/H2O over 30 mins
  4. customto give 15 mg (60%) the title cpd

Sources & evidence

ORD record
ord-163f5eef4d784bec8e40c193fab04d9f
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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