Formamide → HCID 178470649, compound

HRID 1526489Notes

Reaction equation

HRID 1526489 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].[CH:22]([NH2:24])=O>>[OH:8][C:7]1[C:6]2[C:5]3[CH2:12][CH:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:15][C:4]=3[S:3][C:2]=2[N:1]=[CH:22][N:24]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 86695164HCID 86695164, compound

Product 1

HCID 178470649HCID 178470649, compoundYield 52%

Procedure

A solution of ethyl 2-amino-5-(2-ethoxy-2-oxoethyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (20.68 g, 66.41 mmol, 1.00 equiv) in 100 mL of formamide was stirred overnight at 180° C. in an oil bath. After the starting material disappeared, the reaction was cooled to room temperature and quenched with water, extracted with 3×200 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:2) to afford ethyl 2-[3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetate (10.10 g, 52%) as yellow oil. LC-MS (ES, m/z): 293 [M+H]+.

Workup

  1. customquenched with water
  2. extractionextracted with 3×200 mL of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:2)

Sources & evidence

ORD record
ord-795850ea551d4561854d682f8e516328
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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