Water → 2-Amino-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile

HRID 2092261Notes

Reaction equation

HRID 2092261 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[C:17]([CH2:19][OH:20])[N:18]=2)=[CH:10][CH:9]=1.[NH2:21][C:22]1[C:27]([C:28]#[N:29])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][OH:39])=[CH:32][CH:31]=2)[C:25]([C:40]#[N:41])=[C:24](SC2C=CC=CC=2)[N:23]=1.O>COCCOC.C(O)(=O)C>[NH2:21][C:22]1[C:27]([C:28]#[N:29])=[C:26]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][OH:39])=[CH:34][CH:35]=2)[C:25]([C:40]#[N:41])=[C:24]([O:20][CH2:19][C:17]2[N:18]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=3)[O:15][CH:16]=2)[N:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 15555159HCID 15555159, compoundHCID 23665647Potassium tert-butoxideHCID 66630499HCID 66630499, compound

Product 1

HCID 666721372-Amino-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

72 mg (0.64 mmol) of potassium tert-butoxide are suspended in 1 ml of dry 1,2-dimethoxyethane. In succession, 270 mg (1.29 mmol) of the compound from Example 100A and 50 mg (0.13 mmol) of the compound from Example 99A are then added. The reaction mixture is stirred at 60° C. for 2 h and then cooled to RT and stirred at this temperature for a further 8 h. 5 ml of water and 1 ml of 2 N acetic acid are then added to the mixture. A precipitate is formed, which is filtered off with suction and purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Removal of the solvent on a rotary evaporator gives the product as a yellow solid.

Workup

  1. temperaturecooled to RT
  2. stirringstirred at this temperature for a further 8 h
  3. customA precipitate is formed
  4. filtrationwhich is filtered off with suction
  5. custompurified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  6. customRemoval of the solvent
  7. customon a rotary evaporator

Sources & evidence

ORD record
ord-c55d9c06480948bb8aa1e6d66c8d961a
Source dataset
uspto-grants-2013_05
Patent number
US08440700B2

Reaction notes

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