Pyridine → 4-(5-Chloro-2-(((3,3-diphenylpropyl)(2-(4-tetrahydropyranyl)ethyl)carbamoyl)amino)-1,3-thiazol-4-yl)benzenesulfonamide

HRID 2190354Notes

Reaction equation

HRID 2190354 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Cl:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[N:6]=1.N1C=CC=CC=1.[C:24]1([O:30]C(Cl)=O)C=CC=CC=1.CN1CCCC1.[C:40]1([CH:46]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH2:47][CH2:48][NH:49][CH2:50][CH2:51][CH:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C>[Cl:17][C:4]1[S:3][C:2]([NH:1][C:24](=[O:30])[N:49]([CH2:48][CH2:47][CH:46]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:50][CH2:51][CH:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)=[N:6][C:5]=1[C:7]1[CH:8]=[CH:9][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 84541-MethylpyrrolidineHCID 15891Phenyl chloroformateHCID 575863244-(2-Amino-5-chlorothiazol-4-yl)benzenesulfonamideHCID 575863843,3-diphenyl-N-(2-(tetrahydro-2H-pyran-4-yl)ethyl)propan-1-amine

Product 1

HCID 575863864-(5-Chloro-2-(((3,3-diphenylpropyl)(2-(4-tetrahydropyranyl)ethyl)carbamoyl)amino)-1,3-thiazol-4-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2-amino-5-chlorothiazol-4-yl)benzenesulfonamide (0.100 g, 0.35 mmol) and pyridine (0.084 ml, 1 mmol) in 1 ml DMF was cooled to 0° C. and phenylcarbonochloridate (0.041, 0.33 mmol) was added dropwise. The mixture was warmed to room temperature and stirred for 2 hours. At this point 1-methylpyrrolidine (0.11, 1 mmol) and 3,3-diphenyl-N-(2-(tetrahydro-2H-pyran-4-yl)ethyl)propan-1-amine (0.11 g, 0.33 mmol) were added to the reaction mixture consecutively. The reaction mixture was heated to 60° C. and stirred overnight after which it was cooled to room temperature and purified directly over silica (eluted with 0-50% Ethylacetate in hexanes) to give 4-(5-chloro-2-(((3,3-diphenylpropyl)(2-(4-tetrahydropyranyl)ethyl)carbamoyl)amino)-1,3-thiazol-4-yl)benzenesulfonamide. LC-MS ESI (pos.) m/e: 638.8 (M+1).

Workup

  1. temperatureThe reaction mixture was heated to 60° C.
  2. stirringstirred overnight after which it
  3. temperaturewas cooled to room temperature
  4. custompurified directly over silica (eluted with 0-50% Ethylacetate in hexanes)

Sources & evidence

ORD record
ord-6aaf9fafd7ca4813ae34a171dbe31658
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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