HCID 10223485, compound → HCID 10223532, compound

HRID 1167776Notes

Reaction equation

HRID 1167776 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13](=[O:23])[C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH2:20]NC)[CH:15]=3)[S:11][C:7]=2[C:6]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:5][CH:4]=1.[CH3:30][O-:31].[Na+].ClCCl.CO>O1CCCC1>[CH3:30][O:31][CH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][N:17]=1)[C:13]([NH:12][C:10]1[S:11][C:7]2[C:6]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1)=[O:23]

Participants

5

Reactant 3

HCID 10223485HCID 10223485, compoundHCID 10942334Sodium MethoxideHCID 21226129Dichloromethane methanol

Product 1

HCID 10223532HCID 10223532, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-2-methylaminomethyl-isonicotinamide (200 mg, 0.48 mmol, dissolved in tetrahydrofurane (5.0 ml), is treated with sodium methoxide (81 mg, 1.4 mmol) at 0° C. and the mixture heated to 50° C. for 15 h. The mixture is quenched with saturated sodium carbonate (4.0 ml), extracted four times with each 15 ml dichloromethane and the combined organic phases dryed and evaporated. Flash chromatography (first SiO2, eluent: dichloromethane/methanol 0 to 5% and second dichloromethane/ethyl acetae 30% to 60%) afforded the title compound as light yellow crystals (49 mg, 25% yield). MS: m/e=415 (M+H+).

Workup

  1. customThe mixture is quenched with saturated sodium carbonate (4.0 ml)
  2. extractionextracted four times with each 15 ml dichloromethane
  3. customevaporated

Sources & evidence

ORD record
ord-d5f51701241245f8a1e26c6637a50786
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

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