Sodium Methoxide → HCID 67304654, compound

HRID 1008956Notes

Reaction equation

HRID 1008956 reaction equation
[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[CH2:5][CH2:6][NH:7][C:8]1[NH:13][C:12]2[CH:14]=[CH:15][S:16][C:11]=2[C:10](=[O:17])[C:9]=1C(O)=O)[CH3:2].C[O-].[Na+:26]>>[CH2:22]([O:21][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]2[CH:14]=[CH:15][S:16][C:11]2=[C:10]([O-:17])[CH:9]=1)[CH3:23].[Na+:26]

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 67303914HCID 67303914, compound

Product 1

HCID 67304654HCID 67304654, compound

Procedure

5-(3,3-Diethoxypropylamino)-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylic acid (432 g, 1.27 mol) was mixed with sodium methoxide (95% pure, 75.8 g, 1.33 mol) and suspended in xylenes (2 L). The resultant mixture was heated at reflux for 2 h. The reaction mixture was gradually cooled to room temperature with stirring to afford light brown solids. The solids were collected by filtration and washed with toluene and dried under vacuum at 50-60° C. for 48 h to give the desired intermediate sodium 5-(3,3-diethoxypropylamino)thieno[3,2-b]pyridin-7-olate (a solid). This crude product was used in the next step without further purification. 1H NMR (400 MHz, DMSO d6) δ 1.08 (m, 6H), 1.72 (q, 2H, J=6.8 Hz), 3.15 (m, 2H), 4.55 (t, 1H, J=6 Hz), 6.22 (s, 1H), 6.98 (d, 1H, J=5.2 Hz), 7.53 (d, 1H, J=5.2 Hz).

Workup

  1. temperatureat reflux for 2 h
  2. customto afford light brown solids
  3. filtrationThe solids were collected by filtration
  4. washwashed with toluene
  5. customdried under vacuum at 50-60° C. for 48 h

Sources & evidence

ORD record
ord-9191a953a2c14da4bf37f328f9ce68a4
Source dataset
uspto-grants-2011_07
Patent number
US07973050B2

Reaction notes

Loading…