Diisopropylethylamine → N,N'-bis(tert-butoxycarbonyl)-N''-(2-methyl-5-(4-methylpyridin-2-yl)phenyl)guanidine

HRID 1059979Notes

Reaction equation

HRID 1059979 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=2)=[CH:5][C:3]=1[NH2:4].[C:16]([O:20][C:21]([NH:23][C:24]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=S)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(C(C)C)CC)(C)C.[I-].C[N+]1C=CC=CC=1Cl>ClCCl>[C:30]([O:29][C:27]([NH:26][C:24]([NH:23][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])=[N:4][C:3]1[CH:5]=[C:6]([C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=2)[CH:7]=[CH:8][C:2]=1[CH3:1])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 18667479HCID 18667479, compound

Product 1

HCID 135710940N,N'-bis(tert-butoxycarbonyl)-N''-(2-methyl-5-(4-methylpyridin-2-yl)phenyl)guanidineYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-methyl-5-(4-methylpyridin-2-yl)aniline (285 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (475 mg) and diisopropylethylamine (0.577 ml) in dichloromethane (15 ml) was added 1-methyl-2-chloropyridinium iodide (478 mg), and the mixture was stirred for 2 hours. The mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. To the residue was added 2-propanol, and the mixture was stirred. The precipitate was collected by filtration and dried to give N,N′-bis(tert-butoxycarbonyl)-N″-(2-methyl-5-(4-methylpyridin-2-yl)phenyl)guanidine (527 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. additionTo the residue was added 2-propanol
  5. stirringthe mixture was stirred
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-58d42800ee9d44b39786fcfbb4afd508
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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