4-Aminopyridine → HCID 59335034, compound

HRID 1517934Notes

Reaction equation

HRID 1517934 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(C(C)C)CC)(C)C.[C:39](Cl)(Cl)=[O:40].[NH2:43][C:44]1[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=1.[H-].[Na+]>ClCCl.C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:39](=[O:40])[NH:43][C:44]2[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=2)[CH2:17][CH2:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

9

Reactant 5

HCID 17274-AminopyridineHCID 6371PhosgeneHCID 24758Sodium hydrideHCID 81531DiisopropylethylamineHCID 59334895HCID 59334895, compound

Product 1

HCID 59335034HCID 59335034, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

215 mg tert.butyl [(3,5-dichloro-phenylsulphonyl)-(2,3-dihydro-1H-indol-5-yl)-amino]-acetate are dissolved in 10 ml dichloromethane. For this 75 μl diisopropylethylamine and 1 ml of a 20% solution of phosgene in toluene are added. The mixture is stirred for another 2 hours and then the solvents are eliminated in a nitrogen current. The residue is taken up in 10 ml of tetrahydrofuran. To this is added a solution prepared by the addition of 75 mg 4-aminopyridine to a solution of 30 mg sodium hydride (60% suspension in mineral oil) in 10 ml of tetrahydrofuran and 30 minutes' stirring. The mixture is stirred overnight at ambient temperature and then refluxed for 24 hours. The solvents are eliminated in vacuo and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 10:1 to 1:3).

Workup

  1. additionTo this is added a solution
  2. stirringstirring
  3. stirringThe mixture is stirred overnight at ambient temperature
  4. temperaturerefluxed for 24 hours
  5. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 10:1 to 1:3)

Sources & evidence

ORD record
ord-b80ff327426046b68810f063374420f4
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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