Triethylamine → HCID 178428869, compound

HRID 548525Notes

Reaction equation

HRID 548525 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.[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>[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]([C:21]2[CH:22]=[N:23][N:24]([CH3:25])[C:20]=2[OH:19])=[O:10])[CH2:2][CH2:3]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 178481816HCID 178481816, compound

Product 1

HCID 178428869HCID 178428869, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 0.50 g (1.9 mmol) of 3-cyclopropylamino-2-methyl-4-(methylsulfonyl)benzoic acid, 0.24 g (2.4 mmol) of 5-hydroxy-1-methylpyrazole and 0.43 g (2.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were dissolved in dry CH3CN. The mixture was stirred at RT for 5 h. 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 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 extracted with CH2Cl2. The organic phases were dried over MgSO4, and the solvent was removed under reduced pressure. The residue was purified by preparative HPLC. This gave 0.19 g of a beige solid of a purity of 90%.

Workup

  1. stirringthe mixture was stirred at RT for 1 day
  2. customThe solvent was removed under reduced pressure
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. dry with materialThe organic phases were dried over MgSO4
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-062ac8253ba247b99c1a5da4f7fd9318
Source dataset
uspto-grants-2011_05
Patent number
US07943550B2

Reaction notes

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