Sodium methanethiolate → HCID 178427959, compound

HRID 656635Notes

Reaction equation

HRID 656635 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[S:19][C:10]3=[N:11][C:12]([O:17]C)=[C:13]([Cl:16])[C:14]([CH3:15])=[C:9]3[C:8]=2[NH2:20])=[O:6])[CH2:3][CH2:2]1.C[S-].[Na+]>CN(C=O)C>[CH:1]1([NH:4][C:5]([C:7]2[S:19][C:10]3=[N:11][C:12]([OH:17])=[C:13]([Cl:16])[C:14]([CH3:15])=[C:9]3[C:8]=2[NH2:20])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 11536903LY-2033298

Product 1

HCID 178427959HCID 178427959, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-amino-5-chloro-6-methoxy-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (5.0 g, 16.04 mmol) in DMF (45 ml) is added solid 95% sodium thiomethoxide (1.30 g, 17.64 mmol). The reaction vessel is sealed and heated at 100° C. for 5 hours. The reaction is cooled to room temperature and quenched by the addition of water (75 ml). The mixture is acidified to pH2 by the addition of 5N HCl. Gradually, a thick, white precipitate is formed, which is stirred at 0° C. for 10 minutes, then collected by filtration. The solid is dried in the vacuum oven overnight at 60° C. to afford the title compound as a white solid (4.13 g, 86%). Mass (m/z): 298.0 (M++1).

Workup

  1. customThe reaction vessel is sealed
  2. temperatureThe reaction is cooled to room temperature
  3. customquenched by the addition of water (75 ml)
  4. additionThe mixture is acidified to pH2 by the addition of 5N HCl
  5. customGradually, a thick, white precipitate is formed
  6. filtrationcollected by filtration
  7. customThe solid is dried in the vacuum oven overnight at 60° C.

Sources & evidence

ORD record
ord-a9eaa061944b4dca9ddb4deb6354c086
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

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