Water → HCID 22320676, compound

HRID 498083Notes

Reaction equation

HRID 498083 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].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.O.C(OCC)(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([N:5]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[O:19])=[CH:16][CH:15]=1)[O:6][Si:7]([C:10]([CH3:12])([CH3:11])[CH3:13])([CH3:9])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 104392-AminopyridineHCID 113707224-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-benzoic acid

Product 1

HCID 22320676HCID 22320676, compoundYield 186.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g (3.09 mmol) of compound 2 in CH2Cl2 (5 mL) were added 0.733 g (3.71 mmol) of 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride, 0.189 g (1.545 mmol) of 4-dimethylaminopyridine, and 0.438 g (4.63 mmol) of 2-aminopyridine. After stirring for 12 hours at room temperature, H2O and ethyl acetate were added. The organic layer was separated, washed with sat'd NaHCO3 solution, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=10:1) to give 2.3 g of compound 5 in 75% yield.

Workup

  1. customThe organic layer was separated
  2. washwashed with sat'd NaHCO3 solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography (silica, Hex:EtOAc=10:1)

Sources & evidence

ORD record
ord-b2a3804706a747d49165e5217ab6ade2
Source dataset
uspto-grants-2005_09
Patent number
US06949654B2

Reaction notes

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