Acetic Anhydride → HCID 10203366, compound

HRID 1837091Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[C:15](=[O:19])[NH:16][N:17]([CH3:18])[C:13]=3[NH:12][C:11]3[CH2:20][O:21][CH2:22][C:23](=[O:24])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([N:16]1[C:15](=[O:19])[C:14]2[CH:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[CH:3]=3)[C:10]3[C:23](=[O:24])[CH2:22][O:21][CH2:20][C:11]=3[NH:12][C:13]=2[N:17]1[CH3:18])(=[O:27])[CH3:26]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 9908610HCID 9908610, compound

Product 1

HCID 10203366HCID 10203366, compound

Procedure

The product from Example 26C (0.1 g) was heated for 15 minutes on a steam bath with 5 mL of acetic anhydride. The reaction mixture was evaporated under reduced pressure and the residue was chromatographed on silica gel eluting with 5% ethanol/methylene chloride to provide 0.035 g of the title compound as the more polar compound. 1H NMR (DMSO-d6) δ 2.12 (s, 3H), 3.55 (s, 3H), 4.0 (m, 2H), 4.56 (q, 2H), 4.89 (s, 1H), 7.15 (m, 1H), 7.22 (t, 1H), 7.35 (dd, 1H), 10.18 (s, 1H); MS (ESI−) m/z 436 (M−H)−; Anal. Calcd for C18H15N3BrFO4: C, 49.58; H, 3.47; N, 9.63. Found: C, 49.31; H, 3.32; N, 9.62.

Workup

customThe reaction mixture was evaporated under reduced pressure
customthe residue was chromatographed on silica gel eluting with 5% ethanol/methylene chloride

Sources & evidence

ORD record: ord-97f6a4c2265048b4ad79e1625db23eb6
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780872B2

Reaction notes

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