Tetrahydrofuran → N-(Thiazol-2-YL)-6-thioureidopyridine-3-sulfonamide

HRID 1644661Notes

Reaction equation

HRID 1644661 reaction equation
[C:1](Cl)(Cl)=[S:2].[S:5]1[CH:9]=[CH:8][N:7]=[C:6]1[NH:10][S:11]([C:14]1[CH:15]=[N:16][C:17]([NH2:20])=[CH:18][CH:19]=1)(=[O:13])=[O:12].C([N:24](CC)C(C)C)(C)C.O1CCCC1.[OH-].[NH4+]>>[S:5]1[CH:9]=[CH:8][N:7]=[C:6]1[NH:10][S:11]([C:14]1[CH:15]=[N:16][C:17]([NH:20][C:1]([NH2:24])=[S:2])=[CH:18][CH:19]=1)(=[O:12])=[O:13]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 10040ThiophosgeneHCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 575512216-amino-N-(thiazol-2-yl)pyridine-3-sulfonamide

Product 1

HCID 57551257N-(Thiazol-2-YL)-6-thioureidopyridine-3-sulfonamide

Conditions

Temperature
0 °C

Procedure

Carbonothioic dichloride (2.0E1 uL, 0.00026 mol) was added to a solution of the 6-Amino-pyridine-3-sulfonic acid thiazol-2-ylamide (45 mg, 0.00018 mol) and N,N-Diisopropylethylamine (0.092 mL, 0.00053 mol) in Tetrahydrofuran (1.2 mL, 0.014 mol) at 0° C. under an atmosphere of Argon and was stirred for 40 min at 0° C. Saturated ammonium hydroxide solution was added to the reaction mixture and stirred for a few min, then warmed to ambient temperature. The reaction mixture was concentrated and then dried on a lyophilizer to give the crude product that was used in the next step without purification. Note: The starting material, 6-Amino-pyridine-3-sulfonic acid thiazol-2-ylamide, was TFA salts.

Workup

  1. stirringstirred for a few min
  2. temperaturewarmed to ambient temperature
  3. concentrationThe reaction mixture was concentrated
  4. customdried on a lyophilizer

Sources & evidence

ORD record
ord-01e34ce0595d48b2a19590e3b5d27a2e
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

Loading…