1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(tert-butoxycarbonyl)-N'-ethyl-N''-(1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)guanidine

HRID 1059897Notes

Reaction equation

HRID 1059897 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=2)[CH2:3]1.[C:14]([O:18][C:19]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=S)=[O:20])([CH3:17])([CH3:16])[CH3:15].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[C:14]([O:18][C:19]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[N:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=2)[CH2:3]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18622071tert-Butyl (ethylcarbamothioyl)carbamateHCID 18667537HCID 18667537, compound

Product 1

HCID 178464555N-(tert-butoxycarbonyl)-N'-ethyl-N''-(1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)guanidineYield 83.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-1-(4-methylpyridin-2-yl)pyrrolidine (177 mg) and N-(tert-butoxycarbonyl)-N′-ethylthiourea (245 mg) in N,N-dimethylformamide (5 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (230 mg), and the mixture was stirred for 18 hours. The mixture was diluted with ethyl acetate, washed with water three times and brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, 5% methanol in dichloromethane) to give N-(tert-butoxycarbonyl)-N′-ethyl-N″-(1-(4-methylpyridin-2-yl)-pyrrolidin-3-yl)guanidine (290 mg).

Workup

  1. washwashed with water three times and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 25 g, 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f6197ae59ef947c7a4411d2a78813eb9
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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