Water → 4-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamide

HRID 498086Notes

Reaction equation

HRID 498086 reaction equation
[C:1]([N:5]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[NH2:31][C:32]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]2[C:33]=1[CH:34]=[CH:35][CH:36]=[N:37]2.O>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([N:5]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:31][C:32]2[CH:41]=[CH:40][C:39]([OH:42])=[C:38]3[C:33]=2[CH:34]=[CH:35][CH:36]=[N:37]3)=[O:19])=[CH:21][CH:22]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:8])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 113707224-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-benzoic acidHCID 1225379121302-43-2

Product 1

HCID 223207184-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamideYield 35.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.15 g (0.464 mmol) of compound 2 in CH2Cl2 (2 mL) were added 0.11 g (0.561 mmol) of 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride, 0.03 g (0.232 mmol) of 4-dimethylaminopyridine, 2 mL of triethylamine, and 0.16 g (0.695 mmol) of 5-amino-8-hydroxyquinoline HCl salt. After stirring for 24 hours at room temperature, H2O and ethyl acetate were added. The organic layer was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=1:1) to give 0.076 g of compound 9 in 35% yield.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica, Hex:EtOAc=1:1)

Sources & evidence

ORD record
ord-2f8f8a81da3d4b2c91344163eb668f07
Source dataset
uspto-grants-2005_09
Patent number
US06949654B2

Reaction notes

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