Sodium Hydroxide → 3-(Methylsulfanyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carboxamide

HRID 1178699Notes

Reaction equation

HRID 1178699 reaction equation
[CH3:1][S:2][C:3]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:5][N:4]=1.[OH-:17].[Na+]>S(=O)(=O)(O)O>[CH3:1][S:2][C:3]1[C:7]([C:8]([NH2:9])=[O:17])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:5][N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 695154203-(Methylsulfanyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carbonitrile

Product 1

HCID 695158053-(Methylsulfanyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Compound 7 (1.0 g, 4.0 mmol) is dissolved in sulfuric acid (5 mL). The resulting solution is stirred at room temperature for 2 hours, heated to 50° C. for 3.5 hours, then at room temperature for 18 hours, then heated to 50° C. for 1 hour. The reaction was then cooled to room temperature and 1N NaOH (5 mL) was added. The resulting solids were filtered and washed with saturated aqueous sodium bicarbonate to provide 8 (1.15 g, 4.0 mmol). 1H NMR (d6 DMSO): 5 8.12 (2H, d, J=5.8 Hz), 6.78 (2H, d, J=5.8 Hz), 2.32 (3H, s); LRMS (M+): 267.0, (M−): 265.0.

Workup

  1. temperatureheated to 50° C. for 3.5 hours
  2. waitat room temperature for 18 hours
  3. temperatureheated to 50° C. for 1 hour
  4. temperatureThe reaction was then cooled to room temperature
  5. filtrationThe resulting solids were filtered
  6. washwashed with saturated aqueous sodium bicarbonate

Sources & evidence

ORD record
ord-6c7b45d9f85b4d23a594506e16a51389
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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