Dichloromethane → 4-[5-(4-(cyclopropylsulphonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

HRID 41715

Reaction equation

HRID 41715 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClCCl.[CH:33]1([S:36](Cl)(=[O:38])=[O:37])[CH2:35][CH2:34]1>C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27]([S:36]([CH:33]4[CH2:35][CH2:34]4)(=[O:38])=[O:37])[CH2:26][CH2:25]3)=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2760919Cyclopropanesulfonyl chlorideHCID 668637824-(5-(piperazin-1-yl)pyridin-2-yl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

Product 1

HCID 668639214-[5-(4-(cyclopropylsulphonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

10 g of 4-(5-(piperazin-1-yl)pyridin-2-yl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester are placed in a 500 ml round-bottomed flask. 126 ml of dichloromethane are added, followed by 4.23 ml of triethylamine and, finally, 2.7 ml of cyclopropylsulphonyl chloride. The reaction mixture is stirred at ambient temperature for 16 h, then washed with water and once with a saturated sodium chloride solution, dried over magnesium sulphate and then evaporated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of methanol in dichloromethane varying from 0% to 10%. 10.9 g of 4-[5-(4-(cyclopropylsulphonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester are obtained.

Workup

  1. washwashed with water and once with a saturated sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product obtained
  5. customis chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-6d89196070f8439cb3b5da111f665d58
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Linked notes

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