Acetic Anhydride → HCID 25228380, compound

HRID 1920679Notes

Reaction equation

HRID 1920679 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OCC1[CH:19]=[CH:18][C:17]2[C:12](=[C:13]([C:24]#[N:25])[C:14]([O:20][CH2:21][O:22][CH3:23])=[CH:15][CH:16]=2)[N:11]=1>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:5]([O:4][CH2:1][C:2]1[CH:19]=[CH:18][C:17]2[C:12](=[C:13]([C:24]#[N:25])[C:14]([O:20][CH2:21][O:22][CH3:23])=[CH:15][CH:16]=2)[N:11]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 25228246HCID 25228246, compound

Product 1

HCID 25228380HCID 25228380, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Referring to FIG. 20, under a nitrogen atmosphere, DMAP (0.0102 g) and acetic anhydride (0.015 mL, 0.158 mmol) were added to a solution of 10b (0.0090 g, 0.0369 mmol) in chloroform (5 mL) and pyridine (1.5 mL). The reaction was stirred for 24 h. The solvents were evaporated, and the remaining residue was purified by column chromatography (3:7 EtOAc/hexane) to provide 11b (0.0100 g, 0.0351 mmol, 95% yield) as a white solid: 1H NMR (CDCl3) δ 8.16 (1H, d, J=8.0 Hz), 7.98 (1H, d, J=9.2 Hz), 7.55 (1H, d, J=9.2 Hz), 7.44 (1H, d, J=8.4 Hz), 5.46 (2H, s), 5.45 (2H, s), 3.58 (3H, s), 2.26 (3H, s); 13C NMR (CDCl3) δ 170.7, 162.2, 159.2, 148.2, 136.9, 133.5, 122.7, 118.5, 115.7, 114.5, 95.1, 66.7, 56.9, 21.0; FTIR (neat) 2924, 2342, 2224, 1738, 1612, 1508, 1246, 1157, 1070, 937, 846 cm−1; MS (ESI) m/z calculated for (C15H14N2O4+H)+ 287, found 287; HRMS (ESI) m/z calculated for (C15H14N2O4+H)+ 287.1033, found 287.1059.

Workup

  1. customThe solvents were evaporated
  2. customthe remaining residue was purified by column chromatography (3:7 EtOAc/hexane)

Sources & evidence

ORD record
ord-eaf8e5537dc7436fbc0fc59b57590556
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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