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Triethylamine → HCID 178463129, compound

HRID 547248
Notes
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Reaction equation

HRID 547248 reaction equation
[CH2:1]([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)[CH:2]([CH3:4])[CH3:3].[CH2:20]([N:22]1[C:26]([OH:27])=[CH:25][CH:24]=[N:23]1)[CH3:21].Cl.CN(C)CCCN=C=NCC.CCN(CC)CC.[Si](C#N)(C)(C)C.[C-]#N.[K+]>C(#N)C>[CH2:1]([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]([C:25]1[CH:24]=[N:23][N:22]([CH2:20][CH3:21])[C:26]=1[OH:27])=[O:11])[CH:2]([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 82115Trimethylsilyl cyanideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574365663-Isobutylamino-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178418331HCID 178418331, compound

Product 1

HCID 178463129HCID 178463129, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 0.43 g (1.5 mmol) of 3-isobutylamino-2-methyl-4-(methyl-sulfonyl)benzoic acid, 0.22 g (2.0 mmol) of 1-ethyl-5-hydroxypyrazole and 0.35 g (1.8 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. 0.42 ml (3.0 mmol) of NEt3, 0.08 ml (0.6 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, 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. This gave 0.16 g of a red solid of a purity of 96%.

Workup

  1. waitto stand for 2 days
  2. stirringthe mixture was stirred at RT for 2 days
  3. customThe solvent was removed
  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

Sources & evidence

ORD record
ord-181208586dc74e1dbd3c9f8b4c493306
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07939467B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes