Diisopropylethylamine → HCID 135710953, compound

HRID 1059913Notes

Reaction equation

HRID 1059913 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[C:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])=[N:5][CH:6]=[CH:7][CH:8]=1.[C:18]([O:22][C:23]([NH:25][C:26]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=S)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(N(C(C)C)CC)(C)C.[I-].C[N+]1C=CC=CC=1Cl>ClCCl.C(OCC)(=O)C>[C:32]([O:31][C:29]([NH:28][C:26]([NH:25][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])=[N:12][C:11]1[CH:13]=[CH:14][CH:15]=[C:9]([C:4]2[C:3]([C:2]([F:1])([F:16])[F:17])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH:10]=1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 18631012HCID 18631012, compound

Product 1

HCID 135710953HCID 135710953, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(3-trifluoromethylpyridin-2-yl)aniline (200 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (278 mg) and diisopropylethylamine (0.336 ml) in dichloromethane (10 ml) was added 1-methyl-2-chloropyridinium iodide (279 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-trifluoromethylpyridin-2-yl)phenyl)guanidine (234 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-c7b0d76487e940f981c90fe1c50e0749
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

Loading…