2-Methoxyethanol → HCID 86588726, compound

HRID 1167775Notes

Reaction equation

HRID 1167775 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[CH3:8][O:9][C:10]1[C:15]2[N:16]=[C:17]([NH:19][C:20](=[O:30])[C:21]3[CH:26]=[CH:25][N:24]=[C:23]([CH2:27]NC)[CH:22]=3)[S:18][C:14]=2[C:13]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:12][CH:11]=1.ClCCl.CO>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][N:24]=1)[C:20]([NH:19][C:17]1[S:18][C:14]2[C:13]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[CH:12][CH:11]=[C:10]([O:9][CH3:8])[C:15]=2[N:16]=1)=[O:30]

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 10223485HCID 10223485, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 86588726HCID 86588726, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxyethanol (2.6 ml, 48 mmol) is treated at 0° C. with sodium hydride (38 mg, 0.95 mmol, 60% in mineral oil) and the remaining solution allowed to warm to ambient temperature over 1 h. N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-2-methylaminomethyl-isonicotinamide (200 mg, 0.48 mmol, dissolved in tetrahydrofurane (2.0 ml), is added and the mixture stirred at 80° C. for 15 h. The mixture is then evaporated to dryness, treated with saturated sodium carbonate (20 ml) and extracted four times with each 20 ml dichloromethane. The combined organic phases are dryed and evaporated. Flash chromatography (SiO2, eluent: dichloromethane/methanol 20:0 to 19:1) afforded the title compound as light yellow crystals (104 mg, 48% yield). MS: m/e=459 (M+H+).

Workup

  1. additionis added
  2. customThe mixture is then evaporated to dryness
  3. additiontreated with saturated sodium carbonate (20 ml)
  4. extractionextracted four times with each 20 ml dichloromethane
  5. customevaporated

Sources & evidence

ORD record
ord-eb497a193de94acea61e18d3d93277d9
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

Loading…