Pyridine → 1-Cyano-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane

HRID 987128Notes

Reaction equation

HRID 987128 reaction equation
[C:1]([CH:4]([O:29][CH2:30][CH3:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)(=O)[NH2:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1>[C:1]([CH:4]([O:29][CH2:30][CH3:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 229884671-Carbamoyl-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane

Product 1

HCID 229884631-Cyano-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethaneYield 77.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Carbamoyl-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane(0.63 g, 1.47 mmole) was dissolved in dioxane (20 ml) and pyridine (0.35 g, 4.41 mmole) was added. The mixture was placed in a ultrasonic bath for 5 minutes, then trifluoroacetic acid anhydride (0.37 g, 1.76 mmole) was added. After stirring at room temperature for 16 hours it was checked using HPLC that all the starting material was consumed. Sodium carbonate solution was added and extracted three times with dichloromethane. The organic phase was dried with magnesium sulfate and evaporated. Purification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm) using acetronitrile (70-80%) in ammonium acetate buffer (pH 7) as mobil phase gave 0.47 g (75% yield) of the desired product.

Workup

  1. customwas consumed
  2. additionSodium carbonate solution was added
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. customevaporated
  6. customPurification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm)

Sources & evidence

ORD record
ord-cd42a5e9a1f04f6985bc90d9cc11bced
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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