Triethylamine → HCID 57860356, compound

HRID 1947118Notes

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-37833e7f5f8940e8a54e3aec6d5411f0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399449B2

Reaction notes

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