Dimethylformamide → HCID 11715695, compound

HRID 1442637Notes

Reaction equation

HRID 1442637 reaction equation
CN(C=O)C.O[C:7]1[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]2[N:15]=[C:16]([S:18][CH3:19])[S:17][C:8]=12.O=S(Cl)[Cl:22]>O>[Cl:22][C:7]1[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]2[N:15]=[C:16]([S:18][CH3:19])[S:17][C:8]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178503369HCID 178503369, compound

Product 1

HCID 11715695HCID 11715695, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Compound 1f (34.6 g, 120 mmol), DMF-dimethyl acetal (34.0 mL, 240 mmol, 94% purity) and DMF (200 mL) were combined and heated to 80° C. for 90 minutes. The conversion to the cyclized intermediate, 7-hydroxy-2-methylsulfanyl-thiazolo[4,5-b]pyridine-6-carbonitrile was confirmed by LCMS (MS 298, MH+). The mixture was then cooled to 0° C. and SOCl2 was added dropwise (44 mL, 600 mmol). The reaction mixture was stirred for 2 hrs at ambient temperature. The mixture was then cooled back down to 0° C. and water (approximately 300 mL) was added dropwise. The resulting brown solid was collected by filtration and subsequently washed with water and MeOH to provide 7-chloro-2-methylsulfanyl-thiazolo[4,5-b]pyridine-6-carbonitrile Compound 1g (16.1 g) as a tan solid. 1H NMR (CDCl3) δ 8.82 (s, 1H), 2.91 (s, 3H). MS 242, 244 (MH+), 264, 266 (MNa+).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. additionwas added dropwise
  3. filtrationThe resulting brown solid was collected by filtration
  4. washsubsequently washed with water and MeOH

Sources & evidence

ORD record
ord-4c0a3b60b880401d8637750f7cefca1c
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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