Diisopropylethylamine → N,N'-bis(tert-butoxycarbonyl)-N''-(3-(4-methylpyridin-2-yl)phenyl)guanidine

HRID 1059925Notes

Reaction equation

HRID 1059925 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])[CH:3]=1.[C:15]([O:19][C:20]([NH:22][C:23]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=S)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(N(C(C)C)CC)(C)C.[I-].C[N+]1C=CC=CC=1Cl>ClCCl>[C:29]([O:28][C:26]([NH:25][C:23]([NH:22][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])=[N:11][C:10]1[CH:12]=[CH:13][CH:14]=[C:8]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=2)[CH:9]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 186676162-(3-Aminophenyl)-4-methylpyridine

Product 1

HCID 135710945N,N'-bis(tert-butoxycarbonyl)-N''-(3-(4-methylpyridin-2-yl)phenyl)guanidineYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-(4-methylpyridin-2-yl)aniline (276 mg), N,N′-bis (tert-butoxycarbonyl )thiourea (539 mg) and diisopropylethyl-amine (0.601 ml) in dichloromethane (15 ml) was added 1-methyl-2-chloropyridinium iodide (498 mg), and the mixture was stirred for 2.5 hours. The mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 45 g, n-hexane:ethyl acetate=9:1) to give N,N′-bis(tert-butoxycarbonyl) -N″-(3-(4-methylpyridin-2-yl)phenyl)guanidine (397 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 45 g, n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-02bb010c8e694a0fa4962319badc36b0
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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