Pyridine-3-sulfonyl chloride → HCID 56966501, compound

HRID 1036984Notes

Reaction equation

HRID 1036984 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:20])[CH3:19].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:22]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([NH:18][S:27]([C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)(=[O:29])=[O:28])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 3164136Pyridine-3-sulfonyl chlorideHCID 67290361HCID 67290361, compound

Product 1

HCID 56966501HCID 56966501, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(6-Chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (150 mg, 0.53 mmol) and pyridine-3-sulfonyl chloride (102 mg, 0.63 mmol) were dissolved in pyridine (5 mL). The mixture was stirred at room temperature overnight. The solvent was removed and the residue was purified on column chromatography using petroleum ether/ethyl acetate=5:1 as eluent to afford pyridine-3-sulfonic acid [3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide (73 mg, yield: 39%) as yellow solid. MS (ESI+APCI) M+1=357.2.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on column chromatography

Sources & evidence

ORD record
ord-fcd185a6142c496b900e7694729fe2e2
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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