Glycine methyl ester hydrochloride → HCID 54749369, compound

HRID 1661490Notes

Reaction equation

HRID 1661490 reaction equation
[OH:1][C:2]1[C:3]2[S:20][CH:19]=[CH:18][C:4]=2[N:5]([CH3:17])[C:6](=[O:16])[C:7]=1[C:8]([NH:10][CH2:11][C:12]([O:14]C)=[O:13])=[O:9].Cl.NCC(OC)=O.OC1C2SC=CC=2N(C)C(=O)C=1C(OCC)=O>O1CCOCC1>[OH:1][C:2]1[C:3]2[S:20][CH:19]=[CH:18][C:4]=2[N:5]([CH3:17])[C:6](=[O:16])[C:7]=1[C:8]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[O:9]

Participants

5

Reactant 3

HCID 122755Glycine methyl ester hydrochlorideHCID 5774489183179-00-4HCID 67429156HCID 67429156, compound

Product 1

HCID 54749369HCID 54749369, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-(7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxamido)acetate. A mixture of methyl 2-aminoacetate hydrochloride (291 mg, 2317 μmol) and ethyl 7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxylate (489 mg, 1931 μmol) in 15 mL dioxane was heated to 100° C. in a sealed tube and stirred for 15 hours. The mixture was cooled to room temperature, and the resulting suspension was added dropwise to 100 mL ice-water. The precipitate was collected by filtration, washed with H2O, and dried in vacuo. The solids were triturated with Et2O, collected by filtration, and dried to give a beige solid. Purification of the crude product by flash chromatography (Gradient from hexanes to hexanes/EtOAc=1:1) gave the title compound as a white solid (301 mg). MS (ESI) m/z: Calculated; 296.3: Observed; 297.1. 1H NMR (300 MHz, CDCl3) δ ppm 10.73 (1H, br. s), 7.78 (1H, d, J=5.3 Hz), 7.08 (1H, d, J=5.3 Hz), 4.24 (2H, br. s), 3.79 (3H, s), 3.69 (3H, s)

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with H2O
  4. customdried in vacuo
  5. customThe solids were triturated with Et2O
  6. filtrationcollected by filtration
  7. customdried
  8. customto give a beige solid
  9. customPurification of the crude product by flash chromatography (Gradient from hexanes to hexanes/EtOAc=1:1)

Sources & evidence

ORD record
ord-9563c980e84b4592b9414341124ddac5
Source dataset
uspto-grants-2011_10
Patent number
US08030346B2

Reaction notes

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