4-(Pyridin-2-yl)-1,3-thiazol-2-amine → HCID 86662350, compound

HRID 1482825Notes

Reaction equation

HRID 1482825 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][S:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:2]=1.[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>>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[N:28]=[C:29]([NH:32][C:15](=[O:17])[C:14]2[CH:13]=[CH:12][C:11]([S:8](=[O:9])(=[O:10])[NH:7][C:3]3[CH:2]=[C:1]([CH3:20])[CH:6]=[CH:5][CH:4]=3)=[CH:19][CH:18]=2)[S:30][CH:31]=1

Participants

3

Reactant 2

HCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 25744005HCID 25744005, compound

Product 1

HCID 86662350HCID 86662350, compound

Procedure

4-(N-m-tolylsulfamoyl)benzoic acid (14) (99 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 75-100% EtOAc in hexanes. The resulting solid was triturated with dichloromethane/hexanes to give N-(4-(pyridin-2-yl)thiazol-2-yl)-4-(N-m-tolylsulfamoyl)benzamide as an off white solid. Yield: 24 mg (19%). 1H-NMR: 8.64-8.62 (m, 1H), 8.28 (d, J=8.5 Hz, 2H), 8.02 (d, J=8.0 Hz, 1H), 7.95-7.89 (m, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.36 (ddd, J=7.5, 5.0, 1.0 Hz, 1H), 7.24 (t, J=8.0 Hz, 1H), 7.13 (d, J=7.5 Hz, 1H), 6.98-6.96 (m, 1H), 6.88 (d, J=8.0 Hz, 1H), 3.18 (s, 3H).

Workup

  1. customThe residue was purified
  2. washeluting with 75-100% EtOAc in hexanes
  3. customThe resulting solid was triturated with dichloromethane/hexanes

Sources & evidence

ORD record
ord-6aafbbeec3874aa58fa7a6bf259e7098
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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