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

HRID 1913503Notes

Reaction equation

HRID 1913503 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>C(COC)OC.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 were suspended in 1 ml of dry dimethoxyethane. 270 mg (1.29 mmol) of [2-(4-chlorophenyl)-1,3-oxazol-4-yl]methanol and 50 mg (0.13 mmol) of the compound from Example 48A were then added in succession. The reaction mixture was stirred at 60° C. for 2 h and then cooled to RT and stirred at this temperature for 8 h. 5 ml of water and 1 ml of 2N acetic acid were added to the reaction mixture. A precipitate is formed, which was filtered off with suction. The residue was 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 gave the product as a solid.

Workup

  1. temperaturecooled to RT
  2. stirringstirred at this temperature for 8 h
  3. customA precipitate is formed
  4. filtrationwhich was filtered off with suction
  5. customThe residue was purified 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-82621e7d1b1c431f80becee4430062cd
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

Loading…