Diisopropylethylamine → HCID 11960148, compound

HRID 2401046Notes

Reaction equation

HRID 2401046 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[C:23]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][CH:21]=[CH:20][N:19]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1.CCN(C(C)C)C(C)C>CN(C)C=O.O>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[C:23]([N:24]3[CH2:29][CH2:28][N:27]([CH2:32][C:33]4[CH:42]=[CH:41][C:40]5[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=5)[N:34]=4)[CH2:26][CH2:25]3)=[N:22][CH:21]=[CH:20][N:19]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 57444253HCID 57444253, compound

Product 1

HCID 11960148HCID 11960148, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-phenoxy-N-(3-piperazin-1-ylpyrazin-2-yl)benzenesulfonamide (411 mg, 1.0 mmol, 1 eq) in dimethylformamide (10 mL) was added 2-(chloromethyl)quinoline hydrochloride (214 mg, 1 mmol, 1 eq) and DIPEA (322 mg, 2.5 mmol, 2.5 eq). The reaction mixture was heated to 50 degrees over 1 hour. The reaction was cooled, diluted with 30 mL of water and extracted with diethyl ether. The organic layer was dried over MgSO4, evaporated and purified by flash chromatography on silica gel eluting with AcOEt and cyclohexane to give pure 4-phenoxy-N-{3-[4-(quinolin-2-ylmethyl)piperazin-1-yl]pyrazin-2-yl}benzenesulfonamide as a yellow solid (419 mg, 0.76 mmol, yield: 76%, 97% HPLC purity).

Workup

  1. temperatureThe reaction mixture was heated to 50 degrees over 1 hour
  2. temperatureThe reaction was cooled
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. custompurified by flash chromatography on silica gel eluting with AcOEt and cyclohexane

Sources & evidence

ORD record
ord-cd603f930c3840fd924c1ee8d9fd8712
Source dataset
uspto-grants-2014_08
Patent number
US08796280B2

Reaction notes

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