Ammonium Hydroxide → HCID 24959825, compound

HRID 1666571Notes

Reaction equation

HRID 1666571 reaction equation
[CH:1]1([C:6]2[S:10][C:9]([NH:11][C:12]([C:14]3[CH:15]=[C:16]([S:21](Cl)(=[O:23])=[O:22])[CH:17]=[CH:18][C:19]=3[F:20])=[O:13])=[N:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+:25].[OH-]>C(Cl)Cl.C1COCC1>[NH2:25][S:21]([C:16]1[CH:17]=[CH:18][C:19]([F:20])=[C:14]([CH:15]=1)[C:12]([NH:11][C:9]1[S:10][C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:7][N:8]=1)=[O:13])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 59591401HCID 59591401, compound

Product 1

HCID 24959825HCID 24959825, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a 20 ml scintillation vial was added 3-{[(5-cyclopentyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}-4-fluorobenzenesulfonyl chloride (190 mg, 0.488 mmol) in a mixed solvent (DCM/THF=3 mL/1 mL). To this was added 1 ml of 7M NH4OH(NH3 28-30% w/w) . The reaction mixture was stirred vigorously at room temperature for two hours. After consumption of the starting material, the reaction solution was concentrated with a rotary evaporator. The product was dissolved with 1.0 mL of DMSO, was purified by using a Gilson preparative HPLC system with a Waters Xterra (C-18) column 100 mm by 50 mm ID, eluting with 1% B to 99% B in 8.5 min, where A=H2O and B=CH3CN pumped at 150 mL/min to yield 5-(aminosulfonyl)-N-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-2-fluorobenzamide (amount 33 mg, 18.2%).

Workup

  1. customAfter consumption of the starting material
  2. concentrationthe reaction solution was concentrated with a rotary evaporator
  3. dissolutionThe product was dissolved with 1.0 mL of DMSO
  4. customwas purified
  5. washeluting with 1% B to 99% B in 8.5 min

Sources & evidence

ORD record
ord-6d1f8900f0fc44879be879948f7b5819
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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