4-(Pyridin-2-yl)-1,3-thiazol-2-amine → HCID 86662352, compound

HRID 1482832Notes

Reaction equation

HRID 1482832 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH3:28])[S:16]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[N:36]=[C:37]([NH2:40])[S:38][CH:39]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH3:28])[S:16]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH:40][C:37]3[S:38][CH:39]=[C:35]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=4)[N:36]=3)=[O:24])=[CH:26][CH:27]=2)(=[O:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 66761498HCID 66761498, compound

Product 1

HCID 86662352HCID 86662352, compound

Procedure

4-(N-(4-(benzyloxy)phenyl)sulfamoyl)benzoic acid (15) (493 mg, 1.24 mmol) was treated with 4-(pyridin-2-yl)thiazol-2-amine (200 mg, 1.13 mmol) using method C. The residue was purified using flash chromatography eluting with 0-8% MeOH in dichloromethane. The resulting solid was triturated with diethyl ether to give 4-(N-(4-(benzyloxy)phenyl)-N-methylsulfamoyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide as an off white solid. Yield: 289 mg (46%). 1H-NMR: 8.62 (d, J=5.0 Hz, 1H), 8.29 (d, J=8.5 Hz, 2H), 8.02 (d, J=8.0 Hz, 1H), 7.94-7.88 (m, 2H), 7.67 (d, J=8.5 Hz, 2H), 7.46-7.31 (m, 6H), 7.04-6.96 (m, 4H), 5.10 (s, 2H), 3.16 (s, 3H).

Workup

  1. customThe residue was purified
  2. washeluting with 0-8% MeOH in dichloromethane
  3. customThe resulting solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-a050295dbd2041ef90e47d23d9b8eef2
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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