Benzenesulfonyl chloride → HCID 59813778, compound

HRID 1925372Notes

Reaction equation

HRID 1925372 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([NH2:26])=[CH:21][CH:20]=[CH:19]2.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([NH:26][S:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:35])=[O:34])=[CH:21][CH:20]=[CH:19]2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 675202746-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

Product 1

HCID 59813778HCID 59813778, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine (50 mg, 0.144 mmol) and benzenesulfonylchloride (25 mg, 0.144 mmol) were dissolved in pyridine (0.6 mL) then stirred at RT for 3 days. The reaction mixture was concentrated under vacuum. The crude material was purified by silica gel chromatography (2% to 4% MeOH in DCM) to give N-(6-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-naphthalenyl)benzenesulfonamide as a tan solid. MS (ESI pos. ion) m/z: 487.1 (+H). Calc'd for C27H22N2O5S−486.55.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe crude material was purified by silica gel chromatography (2% to 4% MeOH in DCM)

Sources & evidence

ORD record
ord-521e1055f16b435ca05a49476617946e
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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