Triethylamine → HCID 178434077, compound

HRID 1925610Notes

Reaction equation

HRID 1925610 reaction equation
[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=O.[CH3:16][N:17]1[C:21]([OH:22])=[CH:20][C:19]([CH3:23])=[N:18]1.Cl.CN(C)CCCN=C=NCC.CCN(CC)CC.[Si](C#N)(C)(C)C.[C-]#N.[K+]>C(#N)C>[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([C:20]1[C:19]([CH3:23])=[N:18][N:17]([CH3:16])[C:21]=1[OH:22])=[O:7]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 82115Trimethylsilyl cyanideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21183144HCID 21183144, compoundHCID 178429390HCID 178429390, compound

Product 1

HCID 178434077HCID 178434077, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 0.50 g (2.2 mmol) of 3-amino-2-methyl-4-(methylsulfonyl)benzoic acid, 0.32 g (2.8 mmol) of 1,3-dimethyl-5-hydroxypyrazole and 0.50 g (2.6 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. 0.61 ml (4.4 mmol) of NEt3, 0.12 ml (0.9 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 and dried over MgSO4, and the solvent was removed under reduced pressure. The residue was crystallized from acetonitrile. The mother liquor was purified by preparative HPLC. This gave 0.10 g in a purity of 97%.

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. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was crystallized from acetonitrile
  8. customThe mother liquor was purified by preparative HPLC

Sources & evidence

ORD record
ord-4b8302772b264941b2ec9533d6bb2b15
Source dataset
uspto-grants-2012_05
Patent number
US08178695B2

Reaction notes

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