Hydrogen Peroxide → 3-(Methanesulfonyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carboxamide

HRID 1178700Notes

Reaction equation

HRID 1178700 reaction equation
[CH3:1][S:2][C:3]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[S:5][N:4]=1.OO.[OH2:20].C(OC(=O)C)(=[O:23])C>C(O)(=O)C>[CH3:1][S:2]([C:3]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[S:5][N:4]=1)(=[O:23])=[O:20]

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 7918Acetic AnhydrideHCID 695158053-(Methylsulfanyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carboxamide

Product 1

HCID 695159803-(Methanesulfonyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 8 (500 mg, 1.88 mmol) is slurried in acetic anhydride (1.25 mL) and acetic acid (1.25 mL). Hydrogen peroxide (30%, 0.532 mL, 4.7 mmol) is added and stirred for 1 hour. Additional hydrogen peroxide (30%, 0.532 mL, 4.7 mmol) is then added and the reaction is stirred for 1 hour. Water (about 15 mL) is added and the solids were filtered and further dried in vacuo. These solids were determined to be mainly 3-Methanesulfinyl-5-(pyridin-4-ylamino)-isothiazole-4-carboxylic acid amide. The solids are thus re-combined with the mother liquor and acetic anhydride (2.0 mL), acetic acid (2.0 mL) and hydrogen peroxide (30%, 2 mL) are added and stirred for 18 hours at room temperature. The reaction was then extracted with ethyl acetate (15 mL×3) and the combined organics were dried over sodium sulfate, then filtered and concentrated in vacuo obtain crude 3-Methanesulfonyl-5-(pyridin-4-ylamino)-isothiazole-4-carboxylic acid amide (9) (170 mg).

Workup

  1. stirringthe reaction is stirred for 1 hour
  2. filtrationthe solids were filtered
  3. customfurther dried in vacuo
  4. additionare added
  5. stirringstirred for 18 hours at room temperature
  6. extractionThe reaction was then extracted with ethyl acetate (15 mL×3)
  7. dry with materialthe combined organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46d431fb506144a0933ac37f83ea1baa
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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