4-(Pyridin-2-yl)-1,3-thiazol-2-amine → HCID 4853590, compound

HRID 1397928Notes

Reaction equation

HRID 1397928 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH3:22])[S:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:30]=[C:31]([NH2:34])[S:32][CH:33]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH3:22])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:34][C:31]2[S:32][CH:33]=[C:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=3)[N:30]=2)=[O:18])=[CH:20][CH:21]=1)(=[O:11])=[O:12]

Participants

3

Reactant 2

HCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 23601994-[[(2-Methoxyphenyl)methylamino]sulfonyl]benzoic acid

Product 1

HCID 4853590HCID 4853590, compound

Procedure

4-(N-(2-methoxyphenyl)-N-methylsulfamoyl)benzoic acid (13) (109 mg, 0.34 mmol) was treated with 4-(pyridin-2-yl)thiazol-2-amine (50 mg, 0.28 mmol) using method C. The residue was purified using flash chromatography eluting with 50-100% EtOAc in hexanes. The resulting solid was triturated with diethyl ether to give 4-(N-(2-methoxyphenyl)-N-methylsulfamoyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide as an off white solid. Yield: 46 mg (34%). 1H-NMR: 8.65-8.62 (m, 1H), 8.27 (d, J=8.5 Hz, 2H), 8.03 (d, J=7.5 Hz, 1H), 7.95-7.89 (m, 2H), 7.77 (d, J=8.5 Hz, 2H), 7.38-7.32 (m, 2H), 7.22 (dd, J=7.5, 1.5 Hz, 1H), 7.01-6.94 (m, 2H), 3.34 (s, 3H), 3.18 (s, 3H).

Workup

  1. customThe residue was purified
  2. washeluting with 50-100% EtOAc in hexanes
  3. customThe resulting solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-c9d80ed0660a4dd49d164874b94fd5ad
Source dataset
uspto-grants-2014_12
Patent number
US08901306B2

Reaction notes

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