Triethylamine → HCID 19600240, compound

HRID 611255Notes

Reaction equation

HRID 611255 reaction equation
[O:1]1[C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[C:14]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl>[C:14]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([N:7]2[CH2:8][CH2:9][C:4]3[CH:3]=[C:2]([C:10]([O:12][CH3:13])=[O:11])[O:1][C:5]=3[CH2:6]2)=[O:27])=[CH:29][CH:30]=1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 691474-Benzoylbenzoic acidHCID 76257Diethyl cyanophosphonateHCID 19600098Methyl 4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylate

Product 1

HCID 19600240HCID 19600240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 72 mg (0.40 mmol) of methyl 4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-carboxylate, 0.11 g (0.48 mmol) of 4-benzoylbenzoic acid and 0.11 ml (0.79 mmol) of triethylamine in 30 ml of dichloromethane, 0.07 ml (0.48 mmol) of diethyl cyanophosphonate was added dropwise at room temperature, followed by overnight stirring. After the reaction mixture was evaporated under reduced pressure, the resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to yield the desired product.

Workup

  1. customAfter the reaction mixture was evaporated under reduced pressure
  2. customthe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-5b6258c816434dd9bbb6120e933332e1
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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