Acetyl chloride → N-[2-(Quinolin-8-ylsulfamoyl)-5-trifluoromethyl-phenyl]-acetamide

HRID 513594Notes

Reaction equation

HRID 513594 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)(=[O:14])=[O:13].[C:26](Cl)(=[O:28])[CH3:27].CCN(C(C)C)C(C)C>>[N:24]1[C:25]2[C:20](=[CH:19][CH:18]=[CH:17][C:16]=2[NH:15][S:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:7][C:2]=2[NH:1][C:26](=[O:28])[CH3:27])(=[O:13])=[O:14])[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 167595482-Amino-N-quinolin-8-yl-4-trifluoromethyl-benzenesulfonamide2×

Product 1

HCID 68183415N-[2-(Quinolin-8-ylsulfamoyl)-5-trifluoromethyl-phenyl]-acetamideYield 36%

Procedure

In a similar fashion using route 15 general procedure 30, 2-amino-N-(quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide (Example Compound 35) (50 mg, 0.14 mmol), acetyl chloride (9 μl, 0.14 mmol) and DIPEA (59 μl, 0.34 mmol) gave the title compound (20 mg, 36%) after purification by column chromatography with DCM/n-hexane (4:1) as the eluent.

Sources & evidence

ORD record
ord-96fd5167d1b34b0990a048f886ab2cb9
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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