Triethylamine → HCID 57860356, compound

HRID 1513574Notes

Reaction equation

[CH2:1]([C:3]1[N:8]([CH2:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:18])[C:6]2[C:19]([OH:27])=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:21][C:5]=2[CH:4]=1)[CH3:2].[C:28](OCC)(=O)[CH2:29]S.C(N(CC)CC)C>>[CH2:28]([O:27][C:19]1[C:6]2[C:7](=[O:18])[N:8]([CH2:9][C:10](=[O:17])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:3]([CH2:1][CH3:2])=[CH:4][C:5]=2[S:21][C:20]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:29]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 12185Ethyl Thioglycolate

HCID 66893122HCID 66893122, compound

Product 1

HCID 57860356HCID 57860356, compound

Procedure

In the same manner as in Reference Example 5, ethyl 6-ethyl-3-hydroxy-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]pyridine-2-carboxylate was obtained from the compound of Reference Example 39 (3.6 g, 10.3 mmol), ethyl thioglycolate (14.4 mL, 103 mmol) and triethylamine (2.3 mL, 20.6 mmol). The title compound (900 mg, 47%) was obtained as a white solid from the thus-obtained ethyl 6-ethyl-3-hydroxy-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]pyridine-2-carboxylate (1.8 g, 4.7 mmol) by a method similar to that in Reference Example 43.

Sources & evidence

ORD record: ord-b27716bb1e80495eb9ff36d28a1f5d0a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217176B2

Reaction notes

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