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Triethylamine → HCID 178495911, compound

HRID 747542
Notes
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Reaction equation

HRID 747542 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:9]([OH:11])=O.[OH:20][C:21]1[N:25]([CH3:26])[N:24]=[C:23]([CH:27]2[CH2:29][CH2:28]2)[CH:22]=1.[CH3:30]CN=C=NCCCN(C)C.CCN(CC)CC.[Si](C#N)(C)(C)C.[C-]#N.[K+]>CC#N>[CH:27]1([C:23]2[C:22]([C:9]([C:8]3[CH:12]=[CH:13][C:14]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:6]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:30])[C:7]=3[CH3:19])=[O:11])=[C:21]([OH:20])[N:25]([CH3:26])[N:24]=2)[CH2:29][CH2:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 82115Trimethylsilyl cyanideHCID 691167263-[(2-Methoxyethyl)amino]-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178481725HCID 178481725, compound

Product 1

HCID 178495911HCID 178495911, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 0.59 g of crude 3-[(2-methoxyethyl)amino]-2-methyl-4-(methylsulfonyl)benzoic acid was dissolved in 30 ml of CH3CN, and 0.35 g (3 mmol) of 5-hydroxy-3-cyclopropyl-1-methylpyrazole and 0.45 g (2 mmol) of EDAC were then added. The mixture was stirred at RT for one day. 0.36 g (4 mmol) of NEt3, 0.08 g (1 mmol) of Me3SiCN and a spatula tip of KCN were then added, and the mixture was stirred at RT for two days. The mixture was then concentrated, and the residue was taken up in 100 ml of CH2Cl2 and washed with 10% strength H2SO4. The organic phase was dried over MgSO4, concentrated and the residue was purified chromatographically (SiO2, EA/n-heptane=1:1+5% acetic acid). This gave a brown oil.

Workup

  1. stirringthe mixture was stirred at RT for two days
  2. concentrationThe mixture was then concentrated
  3. washwashed with 10% strength H2SO4
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customthe residue was purified chromatographically (SiO2, EA/n-heptane=1:1+5% acetic acid)
  7. customThis gave a brown oil

Sources & evidence

ORD record
ord-2efd1ae87ab44b23846c95781fa36380
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07396939B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes