Diisopropylethylamine → HCID 135710947, compound

HRID 1059973Notes

Reaction equation

HRID 1059973 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=2)=[CH:6][C:4]=1[NH2:5].[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:5][C:4]1[CH:6]=[C:7]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=2)[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 18667649HCID 18667649, compound

Product 1

HCID 135710947HCID 135710947, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-methoxy-5-(4-methylpyridin-2-yl)aniline (294 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (455 mg) and diisopropylethylamine (0.55 ml) in dichloromethane (15 ml) was added 1-methyl-2-chloropyridinium iodide (455 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 70 g, n-hexane:ethyl acetate=3:1) to give N,N′-bis(tert-butoxycarbonyl)-N″-(2-methoxy-5-(4-methylpyridin-2-yl)phenyl)guanidine (334 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 70 g, n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-69d0bd16768945a7892cb2b6f08f0103
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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