Dimethylformamide → HCID 69312679, compound

HRID 902518Notes

Reaction equation

HRID 902518 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH2:7]([O:9][C:10]([C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:15]2[CH:28]=[CH:29][S:30][C:14]=2[C:13]=1O)=[O:11])[CH3:8].CN(C=O)C>C(Cl)Cl>[CH2:7]([O:9][C:10]([C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:15]2[CH:28]=[CH:29][S:30][C:14]=2[C:13]=1[Cl:4])=[O:11])[CH3:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 59702049HCID 59702049, compound

Product 1

HCID 69312679HCID 69312679, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.8 mL, 55 mmol) was added to a solution of 7-hydroxy-4-(4-methoxybenzyl)-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (54) (9.87 g, 27 mmol) in dry CH2Cl2 at 0° C. After adding anhydrous DMF (0.5 mL), the solution was allowed to come at room temperature and was further stirred at room temperature for 24 h. Excess solvent was evaporated to yield 7-chloro-4-(4-methoxybenzyl)-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester as off white solids. Yield 85%; 1H NMR (400 MHz, DMSO-d6) δ 1.30 (t, J=7.2 Hz, 3H), 3.70 (s, 3H), 5.36 (s, 2H), 6.88 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 7.53 (d, J=5.6 Hz, 1H), 8.20 (d, J=5.6 Hz, 1H ppm; MS m/z=378 amu (M++H).

Workup

  1. customto come at room temperature
  2. customExcess solvent was evaporated

Sources & evidence

ORD record
ord-7ff6cc7222124aa9930a0a02e4b7aafe
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

Loading…