Tetrahydrofuran → 3-Amino-pyridine-2-sulfonic acid quinolin-8-ylamide

HRID 513589

Reaction equation

HRID 513589 reaction equation
[NH4+].[Cl-].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][S:14]([C:17]2[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=2)(=[O:16])=[O:15])[CH:6]=[CH:5][CH:4]=1.C1COCC1>CO.[Zn]>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][S:14]([C:17]2[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=2)(=[O:16])=[O:15])[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 681832803-Nitro-pyridine-2-sulfonic acid quinolin-8-ylamide2×

Product 1

HCID 681831363-Amino-pyridine-2-sulfonic acid quinolin-8-ylamideYield 95.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Sat. NH4Cl (0.49 g, 9.09 mmol) was added to a solution of 3-nitro-pyridine-2-sulfonic acid quinolin-8-ylamide (Intermediate 259) (0.3 g, 0.91 mmol) in MeOH:THF(10 ml, 1:1) followed by zinc powder (0.48 g, 7.27 mmol) and the mixture was stirred at room temperature for 18 h. The mixture was filtered through celite and washed with THF. The filtrate was concentrated in vacuo and the residue was diluted with EtOAc. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH as the eluent to give the title compound (0.26 g, 95%)

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe residue was diluted with EtOAc
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with DCM/MeOH as the eluent

Sources & evidence

ORD record
ord-59ab7fdbcc13496aae95b9865214ee63
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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