2-Amino-6-methoxybenzothiazole → HCID 46912956, compound

HRID 1397932Notes

Reaction equation

HRID 1397932 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:22])[S:10]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:5][CH:4]=1.[CH3:23][O:24][C:25]1[CH:34]=[CH:33][C:28]2[N:29]=[C:30]([NH2:32])[S:31][C:27]=2[CH:26]=1>>[CH3:23][O:24][C:25]1[CH:34]=[CH:33][C:28]2[N:29]=[C:30]([NH:32][C:17](=[O:19])[C:16]3[CH:15]=[CH:14][C:13]([S:10](=[O:12])(=[O:11])[N:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[CH3:22])=[CH:21][CH:20]=3)[S:31][C:27]=2[CH:26]=1

Participants

3

Reactant 2

HCID 156302-Amino-6-methoxybenzothiazoleHCID 66762693HCID 66762693, compound

Product 1

HCID 46912956HCID 46912956, compound

Procedure

4-(N-(4-methoxyphenyl)-N-methylsulfamoyl)benzoic acid (7) (100 mg, 0.31 mmol) was treated with 6-methoxybenzo[d]thiazol-2-amine (47 mg, 0.26 mmol) using method C. The residue was purified using flash chromatography eluting with 0-40% EtOAc in hexanes. The resulting solid was triturated with dichloromethane/hexanes to give N-(6-methoxybenzo[d]thiazol-2-yl)-4-(N-(4-methoxyphenyl)-N-methylsulfamoyl)benzamide as a yellow solid. Yield: 26 mg (21%). 1H-NMR: 8.28 (d, J=8.5 Hz, 2H), 7.74-7.61 (m, 4H), 7.08 (dd, J=9.0, 2.5 Hz, 1H), 7.00 (d, J=8.5 Hz, 2H), 6.91-6.88 (m, 2H), 3.83 (s, 3H), 3.74 (s, 3H), 3.16 (s, 3H).

Workup

  1. customThe residue was purified
  2. washeluting with 0-40% EtOAc in hexanes
  3. customThe resulting solid was triturated with dichloromethane/hexanes

Sources & evidence

ORD record
ord-5cbb218ae9b645e8a92a8884da74ebc5
Source dataset
uspto-grants-2014_12
Patent number
US08901306B2

Reaction notes

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