Acetic Anhydride → N-[2-(Quinolin-8-ylsulfamoyl)-phenyl]-acetamide

HRID 513592Notes

Reaction equation

HRID 513592 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].CCN(C(C)C)C(C)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C1COCC1>[N:20]1[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][C:12]=2[NH:11][S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:31](=[O:33])[CH3:32])(=[O:10])=[O:9])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 10701592-Amino-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 68183197N-[2-(Quinolin-8-ylsulfamoyl)-phenyl]-acetamideYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the similar fashion using route 15 general procedure 30, 2-amino-N-(quinolin-8-yl)benzenesulfonamide (Example Compound 8) (100 mg, 0.33 mmol), DIPEA (140 μl, 0.83 mmol), acetic anhydride (23 μl, 0.49 mmol), THF (3 ml) gave the title compound (20 mg, 18%) after purification by column chromatography with DCM/MeOH/NH3 (49:1:1) as the eluent.

Sources & evidence

ORD record
ord-8991fe10153f453cb9ed5a9e2f77bc80
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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