2-Aminothiazole → [4-(Thiazol-2-ylsulfamoyl)-phenyl]-carbamic acid 8-trifluoromethyl-quinolin-4-yl ester

HRID 219554Notes

Reaction equation

HRID 219554 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[OH:13].[N:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)=[C:17]=[O:18].[NH2:29][C:30]1[S:31][CH:32]=[CH:33][N:34]=1>C1COCC1.N1C=CC=CC=1>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[O:13][C:17](=[O:18])[NH:16][C:19]1[CH:24]=[CH:23][C:22]([S:25](=[O:27])(=[O:26])[NH:29][C:30]2[S:31][CH:32]=[CH:33][N:34]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 81230p-Isocyanatobenzenesulphonyl chlorideHCID 1785164428-(Trifluoromethyl)quinolin-4-ol

Product 1

HCID 57936427[4-(Thiazol-2-ylsulfamoyl)-phenyl]-carbamic acid 8-trifluoromethyl-quinolin-4-yl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-trifluoromethyl-quinolin-4-ol (107 mg, 0.50 mmol) in THF (5 mL) was added 4-isocyanatobenzene-sulfonyl chloride (109 mg, 0.50 mmol) at RT. The resulting mixture was stirred at ambient temperature for 1 h. Then, a solution of 2-aminothiazole (50 mg, 0.50 mmol) in pyridine (5 mL) was added and stirring was continued for 65 h. The solvents were evaporated under a stream of nitrogen, the residue was dissolved in DMSO (2 mL) and purified by preparative LC/MS (gradient of 5-95% CH3CN/water). 1H-NMR (DMSO-d6) δ 9.63 (s, 1H), 9.10 (s, 1H) 8.28-8.22 (m, 2H), 7.97-7.95 (m, 2H), 7.81-7.77 (m, 3H), 7.52-7.51 (m, 1H), 7.41-7.40 (m, 2H), 7.15-7.14 (m, 1H). LC/MS (5-95%) M/Z: M+1 obs=495.4; tR=10.45.

Workup

  1. stirringstirring
  2. waitwas continued for 65 h
  3. customThe solvents were evaporated under a stream of nitrogen
  4. dissolutionthe residue was dissolved in DMSO (2 mL)
  5. custompurified by preparative LC/MS (gradient of 5-95% CH3CN/water)

Sources & evidence

ORD record
ord-5ce3b820f85d4ce38e5960ff5d7c1f28
Source dataset
uspto-grants-2012_06
Patent number
US08202861B2

Reaction notes

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