Acetic Anhydride → HCID 23594035, compound

HRID 434069Notes

Reaction equation

HRID 434069 reaction equation
[OH:1][C@H:2]1[C@@H:9]2[N:5]([C:6](=[O:23])[N:7]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[C:8]2=[O:10])[CH2:4][CH2:3]1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:24]([O:1][CH:2]1[CH:9]2[N:5]([C:6](=[O:23])[N:7]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[C:8]2=[O:10])[CH2:4][CH2:3]1)(=[O:26])[CH3:25]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 9944398HCID 9944398, compound

Product 1

HCID 23594035HCID 23594035, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 6C (123 mg, 0.4 mmol) in pyridine (3 mL) was added acetic anhydride (0.26 mL, 2.8 mmol), followed by 4-dimethylaminopyridine (15 mg). The reaction mixture was stirred at RT for 3 h, then quenched with water and extracted with CH2Cl2 (3×10 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give a crude product, which was chromatographed (silica gel) eluting with 2% MeOH in EtOAc/hexane (1:1) to give 70 mg of the title compound (racemate) as a white solid. m.p. 105° C.; HPLC: 99% at 4.8 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 350 [M+1]+.

Workup

  1. customquenched with water
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give a crude product, which
  8. customwas chromatographed (silica gel)
  9. washeluting with 2% MeOH in EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-1a081040050f493d81182c5408b5c47a
Source dataset
uspto-grants-2003_12
Patent number
US06670386B2

Reaction notes

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