Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → HCID 70872462, compound

HRID 1616438Notes

Reaction equation

HRID 1616438 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:20][C:21](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:22]>>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:21](=[O:22])[CH3:20])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 70872676methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate

Product 1

HCID 70872462HCID 70872462, compoundYield 68%

Procedure

A solution of methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate (520 mg, 1.58 mmol) was heated at 70° C. in Acetic 3 ml of anhydride for 6 h. The reaction mixture was cooled to room temperature and quenched with sat. NaHCO3 and extracted with ethyl acetate. The organic layer was dried over Na2SO4, concentrated and purified by silica gel (100-200) column chromatography to get the target compound (400 mg, 68%).

Workup

  1. customquenched with sat. NaHCO3
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel (100-200) column chromatography

Sources & evidence

ORD record
ord-69d6fbe991c74b78a22f825ea84126c8
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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