Ammonia → 6-amino-N-(thiazol-2-yl)pyridine-3-sulfonamide

HRID 1644660Notes

Reaction equation

HRID 1644660 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:11]=[N:12][C:13](Cl)=[CH:14][CH:15]=1)(=[O:9])=[O:8].[NH3:17]>CO>[NH2:17][C:13]1[N:12]=[CH:11][C:10]([S:7]([NH:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)(=[O:9])=[O:8])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 9431916-chloro-N-(1,3-thiazol-2-yl)pyridine-3-sulfonamide

Product 1

HCID 575512216-amino-N-(thiazol-2-yl)pyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-pyridine-3-sulfonic thiazol-2-ylamide (200 mg, 0.0007 mol) in 7 M of Ammonia in methanol (5.00 mL) was heated at 160° C. in a pressure bottle for ˜6 h. The reaction had to be stopped because the pressure was too high and some of the reaction solution was leaking. By LC/MS, reaction show ˜30% conversion. The reaction solution was concentrated and then purified on Gilson (Prep LC, reverse phase, Phenomenex 250×30 mm, 15 micron C18 column, 40 mL/min. Gradient, 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8). Fractions were checked by LC/MS and dried on a lyophilizer to give the product as a brown oil.

Workup

  1. customBy LC/MS, reaction
  2. concentrationThe reaction solution was concentrated
  3. custompurified on Gilson (Prep LC, reverse phase, Phenomenex 250×30 mm, 15 micron C18 column, 40 mL/min. Gradient, 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8)
  4. customdried on a lyophilizer

Sources & evidence

ORD record
ord-eb7f88e94a7e4f4c9256bf2800a20ad8
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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