Triethylamine → Methyl N-(6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl)-N-methylglycinate

HRID 1913505Notes

Reaction equation

HRID 1913505 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([O:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[O:27][CH:28]=2)[N:3]=1.Cl.[NH:37]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH3:38].C(N(CC)CC)C>C1COCC1>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2[O:27][CH:28]=[C:24]([CH2:23][O:22][C:4]3[N:3]=[C:2]([N:37]([CH3:38])[CH2:39][C:40]([O:42][CH3:43])=[O:41])[C:7]([C:8]#[N:9])=[C:6]([C:10]4[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=4)[C:5]=3[C:20]#[N:21])[N:25]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 866496412-Chloro-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]-pyridine-3,5-dicarbonitrile

Product 1

HCID 66672288Methyl N-(6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl)-N-methylglycinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

230 mg (about 0.45 mmol) of the crude product from Example 50A were dissolved in 3 ml of absolute THF, and 127 mg (0.91 mmol) of methyl sarcosinate hydrochloride and 138 mg (1.36 mmol) of triethylamine were added. The reaction mixture was stirred at RT for 10 h. After removal of the solvent on a rotary evaporator, the residue was purified directly 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 white solid.

Workup

  1. customAfter removal of the solvent
  2. customon a rotary evaporator
  3. customthe residue was purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  4. customRemoval of the solvent
  5. customon a rotary evaporator

Sources & evidence

ORD record
ord-085deab682e14926a8856ba10b48100a
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

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