Triethylamine → HCID 178434078, compound

HRID 1925612Notes

Reaction equation

HRID 1925612 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]([CH3:18])=[C:7]([CH:11]=[CH:12][C:13]=2[S:14]([CH3:17])(=[O:16])=[O:15])[C:8]([OH:10])=O)[CH2:3][CH2:2]1.[CH3:19][N:20]1[C:24]([OH:25])=[CH:23][C:22]([CH3:26])=[N:21]1.Cl.CN(C)CCCN=C=NCC.CCN(CC)CC.[Si](C#N)(C)(C)C.[C-]#N.[K+]>C(#N)C>[CH3:19][N:20]1[C:24]([OH:25])=[C:23]([C:8](=[O:10])[C:7]2[CH:11]=[CH:12][C:13]([S:14]([CH3:17])(=[O:16])=[O:15])=[C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)[C:6]=2[CH3:18])[C:22]([CH3:26])=[N:21]1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 82115Trimethylsilyl cyanideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574249453-Cyclopropylamino-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178429390HCID 178429390, compound

Product 1

HCID 178434078HCID 178434078, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 0.50 g (1.9 mmol) of 3-cyclopropylamino-2-methyl-4-(methyl-sulfonyl)benzoic acid, 0.27 g (2.4 mmol) of 1,3-dimethyl-5-hydroxypyrazole and 0.43 g (2.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were dissolved in dry acetonitrile. The mixture was stirred at RT for 1 day and allowed to stand for 2 days. 0.52 ml (3.7 mmol) of NEt3, 0.10 ml (0.7 mmol) of Me3SiCN and a spatula tip of KCN were added, and the mixture was stirred at RT for 2 days. The solvent was removed under reduced pressure, and the residue was taken up in CH2Cl2 and 10% strength H2SO4. The organic phase was separated off, the aqueous phase was extracted once with CH2Cl2, the combined organic phases were dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by preparative HPLC. This gave 0.16 g of a white-beige amorphous solid in a purity of 93%.

Workup

  1. waitto stand for 2 days
  2. stirringthe mixture was stirred at RT for 2 days
  3. customThe solvent was removed under reduced pressure
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was extracted once with CH2Cl2
  6. dry with materialthe combined organic phases were dried over MgSO4
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b876cf92ba1f469db796a18502f1a3da
Source dataset
uspto-grants-2012_05
Patent number
US08178695B2

Reaction notes

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