N,N'-Dimethylethylenediamine → HCID 53627660, compound

HRID 1715968Notes

Reaction equation

HRID 1715968 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]([C@@H:28]1[CH2:32][CH2:31][NH:30][C:29]1=[O:33])[CH2:23][CH2:22][CH2:21]2.CNCCNC.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CO.[Cu]I.CN1C(=O)CCC1>[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]([C@@H:28]1[CH2:32][CH2:31][N:30]([C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]4[S:13][CH:14]=[CH:15][N:16]=4)(=[O:10])=[O:9])=[CH:4][CH:3]=3)[C:29]1=[O:33])[CH2:23][CH2:22][CH2:21]2

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 6693044-bromo-N-(1,3-thiazol-2-yl)benzene-1-sulfonamideHCID 59466376HCID 59466376, compound

Product 1

HCID 53627660HCID 53627660, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Conditions

Temperature
200 °C

Procedure

Prepared using general procedure 64. 4-Bromo-N-(thiazol-2-yl)benzenesulfonamide (54 mg, 0.17 mmol), (R)-3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)pyrrolidin-2-one (50 mg, 0.20 mmol), copper(I) iodide (3.8 mg, 10 mol %), N,N′-dimethylethylenediamine (4.2 μL, 20 mol %), and K2CO3 (94 mg, 0.68 mmol) were combined in a microwave vial and set under nitrogen. NMP (0.4 mL) was added, and the reaction mixture was heated to 200° C. for 30 min. using microwave irradiation. After cooling to RT, the reaction mixture was diluted with DMSO/MeOH (1:1, 0.6 mL) and purified via reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give (R)-4-(3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=489.3; tR=3.27 min.

Workup

  1. customPrepared
  2. custommicrowave irradiation
  3. temperatureAfter cooling to RT
  4. custompurified via reverse phase

Sources & evidence

ORD record
ord-2e49f6827f054472842cf3dee74ec1ae
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

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