Acetic Anhydride → HCID 24821339, compound

HRID 1028473Notes

Reaction equation

HRID 1028473 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([NH2:21])[CH3:20])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([NH:21][C:33](=[O:35])[CH3:34])[CH3:20])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 69189942HCID 69189942, compound

Product 1

HCID 24821339HCID 24821339, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 11D ((110 mg, 0.337 mmol) and diisopropylethylamine (0.5 mL) in methylene chloride (1 mL) cooled to 0° C. was added acetic anhydride (100 μL, 1.06 mmol, 3.1 eq.). The mixture was stirred at room temperature overnight. The reaction mixture was purified directly on silica gel eluting with ethyl acetate:hexane gradient (0-80%) to give the title compound (109 mg, 88%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.30 (d, J=8.09 Hz, 1 H), 7.66 (s, 1 H), 7.45-7.54 (m, 2 H), 7.33-7.40 (m, 2 H), 7.27-7.32 (m, Hz, 2 H), 6.99-7.10 (m, 2 H), 4.77-4.96 (m, 1 H), 3.79 (s, 3 H), 1.83 (s, 3 H), 1.32 (d, J=6.99 Hz, 3 H); MS (DCl) m/e 369 (M+H).

Workup

  1. customThe reaction mixture was purified directly on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-b477421759f44e95a62d600ff3959660
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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