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Diisopropylethylamine → HCID 135710943, compound

HRID 1059947
Notes
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Reaction equation

HRID 1059947 reaction equation
[Si:1]([O:8][C:9]1[C:10]([C:15]2[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=2)[NH2:18])=[N:11][CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:22]([O:26][C:27]([NH:29][C:30]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=S)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(C(C)C)CC)(C)C.[I-].C[N+]1C=CC=CC=1Cl>ClCCl.C(OCC)(=O)C>[C:36]([O:35][C:33]([NH:32][C:30]([NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])=[N:18][C:17]1[CH:19]=[CH:20][CH:21]=[C:15]([C:10]2[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:16]=1)=[O:34])([CH3:39])([CH3:38])[CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 18630991HCID 18630991, compound

Product 1

HCID 135710943HCID 135710943, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(3-tert-butyldimethylsilyloxypyridin-2-yl)-aniline (303 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (335 mg) and diisopropylethylamine (0.405 ml) in dichloromethane (10 ml) was added 1-methyl-2-chloropyridinium iodide (335 mg), and the mixture was stirred for 18 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, 35 g, 20% ethyl acetate in n-hexane) to give N,N′-bis(tert-butoxycarbonyl)-N″-(3-(3-tert-butyldimethylsilyloxypyridin-2-yl)phenyl)guanidine (486 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, 35 g, 20% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-fefb753c5b2c4228b9774b00de7fa6e2
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06521643B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes