Diisopropylethylamine → HCID 135706149, compound

HRID 1059961Notes

Reaction equation

HRID 1059961 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=2[CH3:16])[NH2:12])[CH:4]=1.[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: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:12][C:11]1[CH:13]=[CH:14][C:15]([CH3:16])=[C:9]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][N:6]=2)[CH:10]=1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 18630998HCID 18630998, compound

Product 1

HCID 135706149HCID 135706149, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-(4-methoxypyridin-2-yl)-4-methylaniline (238 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (368 mg) and diisopropylethylamine (0.445 ml) in dichloromethane (10 ml) was added 1-methyl-2-chloropyridinium iodide (369 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. The residue was purified by column chromatography (silica gel 25 g, n-hexane:ethyl acetate=3:1) to give N,N′-bis(tert-butoxycarbonyl)-N″-(3-(4-methoxypyridin-2-yl)-4-methylphenyl)guanidine (471 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 25 g, n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-d8dc7f2ab4c94a098fe9c0e4168ed557
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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