Water → HCID 13481973, compound

HRID 1876019Notes

Reaction equation

HRID 1876019 reaction equation
Cl[C:2]1[C:3]([NH:9][C:10]([NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[S:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C[O-].[Na+].O>CN1C(=O)CCC1>[Cl:8][C:6]1[CH:7]=[C:2]2[S:11][C:10]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:9][C:3]2=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 59286693HCID 59286693, compound

Product 1

HCID 13481973HCID 13481973, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To N-(3,5-dichloropyridin-2-ylcarbamothioyl)benzamide (5.2 g, 16 mmol) in NMP (40 mL) was added sodium methoxide (1.73 g, 32.0 mmol). The mixture was heated in a 120° C. oil bath for 4 h, cooled to ambient temperature and poured into water. The solids were collected by filtration and purified on by silica gel chromatography (0-5% (9:1 MeOH:NH4OH)/chloroform) to give N-(6-chlorothiazolo[4,5-b]pyridin-2-yl)benzamide (364 mg, 1.256 mmol, 7.85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.16 (br. s., 1H) 8.48-8.58 (m, 2H) 8.13-8.23 (m, 2H) 7.61-7.69 (m, 1H) 7.56 (t, J=7.53 Hz, 2H). MS (LC/MS) R.T.=2.8; [M+H]+=290.1.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe solids were collected by filtration
  3. custompurified on by silica gel chromatography (0-5% (9:1 MeOH:NH4OH)/chloroform)

Sources & evidence

ORD record
ord-bc51b982254043928624b9bbe926a502
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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