Triethylamine → HCID 178456804, compound

HRID 548527Notes

Reaction equation

HRID 548527 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]([CH3:18])=[C:7]([CH:11]=[CH:12][C:13]=1[S:14]([CH3:17])(=[O:16])=[O:15])[C:8]([OH:10])=O)[CH:2]=[CH2:3].[OH:19][C:20]1[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=1.Cl.CN(C)CCCN=C=NCC.CCN(CC)CC.[Si](C#N)(C)(C)C.[C-]#N.[K+]>CC#N>[CH2:1]([NH:4][C:5]1[C:6]([CH3:18])=[C:7]([CH:11]=[CH:12][C:13]=1[S:14]([CH3:17])(=[O:16])=[O:15])[C:8]([C:21]1[CH:22]=[N:23][N:24]([CH3:25])[C:20]=1[OH:19])=[O:10])[CH:2]=[CH2:3]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 82115Trimethylsilyl cyanideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574249463-Allylamino-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178481816HCID 178481816, compound

Product 1

HCID 178456804HCID 178456804, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 0.31 g (1.2 mmol) of 3-allylamino-2-methyl-4-(methylsulfonyl)benzoic acid, 0.15 g (1.5 mmol) of 5-hydroxy-1-methylpyrazole and 0.27 g (1.4 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were dissolved in dry CH3CN. The mixture was stirred at RT for 5 h. 0.32 ml (2.3 mmol) of NEt3, 0.06 ml (0.5 mmol) of Me3SiCN and a spatula tip of KCN were added, and the mixture was stirred at RT for 1 day. The solvent was removed under reduced pressure, and the residue was taken up in CH2Cl2 and 10% strength H2SO4. The aqueous phase was removed and extracted once with CH2Cl2. The combined organic phases were dried over MgSO4, and the solvent was removed under reduced pressure. The residue was crystallized from tert-butyl methyl ether. This gave 0.15 g of a colorless solid of a purity of 100%.

Workup

  1. stirringthe mixture was stirred at RT for 1 day
  2. customThe solvent was removed under reduced pressure
  3. customThe aqueous phase was removed
  4. extractionextracted once with CH2Cl2
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was crystallized from tert-butyl methyl ether

Sources & evidence

ORD record
ord-18399ec25e98449d992230372718e691
Source dataset
uspto-grants-2011_05
Patent number
US07943550B2

Reaction notes

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