Water → HCID 178494656, compound

HRID 1724832Notes

Reaction equation

HRID 1724832 reaction equation
O=C1CCC(=O)N1O[C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:18]2[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=2)=[N:15][C:16]=1[NH2:17])=[O:10].CC(C)([O-])C.[K+].[CH3:34][O:35][CH2:36][C:37](=O)[CH2:38][C:39]([O:41][CH3:42])=[O:40].O>C1COCC1>[CH3:42][O:41][C:39]([C:38]1[C:37]([CH2:36][O:35][CH3:34])=[N:17][C:16]2[C:11]([C:9]=1[OH:10])=[CH:12][CH:13]=[C:14]([C:18]1[C:23]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:21]=[CH:20][N:19]=1)[N:15]=2)=[O:40]

Participants

6

Reactant 4

HCID 962WaterHCID 123500Methyl 4-methoxyacetoacetateHCID 23665647Potassium tert-butoxideHCID 59811150HCID 59811150, compound

Product 1

HCID 178494656HCID 178494656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-amino-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (1-0.4 g, 27.3 mmol) in 50 mL dry THF is added in one portion to a mixture of potassium t-butoxide (7.36 g, 65.6 mmol) and methyl 4-methoxy-acetoacetate (8.77 g, 60.7 mmol) in dry THF (100 mL). The reaction is stirred overnight at room temperature. Water (30 mL) is added and the solution concentrated (˜30 mL). The resulting mixture is extracted with ether (2×50 mL). The aqueous portion is acidified with concentrated hydrochloric acid and extracted with CH2Cl2 (4×100 mL). The combined organic extracts are dried over Na2SO4 and the solvent removed under reduced pressure to yield the title compound as a light brown oil that solidifies upon standing.

Workup

  1. concentrationthe solution concentrated (˜30 mL)
  2. extractionThe resulting mixture is extracted with ether (2×50 mL)
  3. extractionextracted with CH2Cl2 (4×100 mL)
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-26f7682c4b9746f0ab8ee6e621b8bd65
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

Loading…