HCID 46941716, compound → Thieno[3,2-c]pyridine-2-carboxylic acid, 4,5,6,7-tetrahydro-3-methyl-, ethyl ester

HRID 468667Notes

Reaction equation

HRID 468667 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C.O=[Pt]=O>[CH3:1][C:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 1

HCID 46941716HCID 46941716, compound

Product 1

HCID 58157568Thieno[3,2-c]pyridine-2-carboxylic acid, 4,5,6,7-tetrahydro-3-methyl-, ethyl esterYield 40%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-methylthieno[3,2-c]pyridine-2-carboxylate (4 g, 0.018 mol) and PtO2 (0.5 g, 0.002 mol) in ethanol (100 mL) was stirred under an H2 atmosphere (3 atmospheres) for 72 hours at room temperature. The PtO2 was removed by filtration, the filtrate was concentrated under reduced pressure and the residue obtained was purified by silica gel chromatography (DCM/EtOH=10:1) to afford ethyl 3-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (1.6 g, 40%). ES+ 226; 1H NMR (400 MHz, DMSO) δ 4.24 (q, J=7.1 Hz, 2H), 3.93 (s, 2H), 3.21 (t, J=5.9 Hz, 2H), 2.89 (t, J=5.7 Hz, 2H), 2.55 (s, 1H), 2.34 (s, 3H), 1.26 (t, J=6.0 Hz, 3H).

Workup

  1. customThe PtO2 was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue obtained
  4. customwas purified by silica gel chromatography (DCM/EtOH=10:1)

Sources & evidence

ORD record
ord-e2ee240d61d24c0a9609394ce36b6225
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Reaction notes

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