Triethylamine → HCID 19600268, compound

HRID 611388Notes

Reaction equation

HRID 611388 reaction equation
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[C:11]1([C:17]2([C:22]3[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=3)[S:21][CH2:20][CH2:19][S:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O.O>[C:11]1([C:17]2([C:22]3[CH:23]=[CH:24][C:25]([C:26]([N:8]4[CH2:9][CH2:10][C:5]5[CH:4]=[CH:3][O:2][C:6]=5[CH2:7]4)=[O:27])=[CH:29][CH:30]=3)[S:21][CH2:20][CH2:19][S:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochlorideHCID 22262276HCID 22262276, compound

Product 1

HCID 19600268HCID 19600268, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.582 g (9.912 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 3.00 g (9.91 mmol) of 4-(2-phenyl-1,3-dithiolan-2-yl)benzoic acid and 5.53 ml (39.6 mmol) of triethylamine in 50 ml of N,N-dimethylformamide, 1.80 ml (11.9 mmol) of diethyl cyanophosphonate was added dropwise, followed by overnight stirring at room temperature. This mixture was poured into water and extracted with diethyl ether 3 times. The combined organic layer was dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 2/1) to yield the desired product.

Workup

  1. extractionextracted with diethyl ether 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 2/1)

Sources & evidence

ORD record
ord-1353c563936b45f5a889466392ac03f2
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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