HCID 69312679, compound → HCID 15565856, compound

HRID 902519Notes

Reaction equation

HRID 902519 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10](CC2C=CC(OC)=CC=2)[C:9]2[CH:22]=[CH:23][S:24][C:8]=2[C:7]=1[Cl:25])=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[NH:10][C:9]2[CH:22]=[CH:23][S:24][C:8]=2[C:7]=1[Cl:25])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 69312679HCID 69312679, compound

Product 1

HCID 15565856HCID 15565856, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-chloro-4-(4-methoxybenzyl)-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (55) (10.40 g, 27.5 mmol) in neat TFA was heated at 70° C. under argon for 36 h. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried to yield 7.08 g (99%) of 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester as white solids. MP 206° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.28 (t, J=7.2 Hz, 3H), 4.29 (q, J=7.2 Hz, 2H), 7.10 (d, J=5.2 Hz, 1H), 8.13 (d, J=5.2 Hz, 1H) ppm; MS m/z=240 amu (M++1).

Workup

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. customdried

Sources & evidence

ORD record
ord-c856f620fd314dba982d8c7be1b11ad7
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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