Diisopropylethylamine → HCID 135706156, compound

HRID 1059916Notes

Reaction equation

HRID 1059916 reaction equation
[N+:1]([C:4]1[C:5]([C:10]2[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=2)[NH2:13])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:17]([O:21][C:22]([NH:24][C:25]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=S)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(C(C)C)CC)(C)C.[I-].C[N+]1C=CC=CC=1Cl>ClCCl.C(OCC)(=O)C>[C:31]([O:30][C:28]([NH:27][C:25]([NH:24][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])=[N:13][C:12]1[CH:14]=[CH:15][CH:16]=[C:10]([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:11]=1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 186676353-(3-Nitropyridin-2-yl)-aniline

Product 1

HCID 135706156HCID 135706156, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(3-nitropyridin-2-yl)aniline (400 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (616 mg) and diisopropylethylamine (0.745 ml) in dichloromethane (18.6 ml) was added 1-methyl-2-chloropyridinium iodide (618 mg), and the mixture was stirred for 16 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 30 g, n-hexane:ethyl acetate=4:1) to give N,N′-bis(tert-butoxycarbonyl)-N″-(3-(3-nitropyridin-2-yl)phenyl)guanidine (730 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 30 g, n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-50607036f42d4136b9b7d2d79bf86c4a
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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