4-(Pyridin-2-yl)-1,3-thiazol-2-amine → HCID 2660525, compound

HRID 1397939Notes

Reaction equation

HRID 1397939 reaction equation
[CH3:1][N:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[S:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[N:28]=[C:29]([NH2:32])[S:30][CH:31]=1>>[CH3:1][N:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[S:3]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:32][C:29]2[S:30][CH:31]=[C:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=3)[N:28]=2)=[O:12])=[CH:13][CH:14]=1)(=[O:4])=[O:5]

Participants

3

Reactant 2

HCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 23772014-[methyl(phenyl)sulfamoyl]benzoic acid

Product 1

HCID 2660525HCID 2660525, compound

Procedure

4-(N-methyl-N-phenylsulfamoyl)benzoic acid (16) (100 mg, 0.31 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-methyl-N-phenylsulfamoyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide as an orange solid. Yield: 31 mg (24%). 1H-NMR: 8.63-8.61 (m, 1H), 8.28 (d, J=8.5 Hz, 2H), 8.02 (d, J=8.0 Hz, 1H), 7.94-7.88 (m, 2H), 7.68 (d, J=8.5 Hz, 2H), 7.40-7.30 (m, 4H), 7.13 (d, J=7.0 Hz, 2H), 3.20 (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-a920b7079ec04c30bc3624817a8b7c25
Source dataset
uspto-grants-2014_12
Patent number
US08901306B2

Reaction notes

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