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Triethylamine → HCID 178467927, compound

HRID 547250
Notes
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Reaction equation

HRID 547250 reaction equation
[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[CH2:5][NH:6][C:7]1[C:8]([CH3:20])=[C:9]([CH:13]=[CH:14][C:15]=1[S:16]([CH3:19])(=[O:18])=[O:17])[C:10]([OH:12])=O)[CH3:2].[OH:24][C:25]1[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=1.Cl.[CH3:32]N(C)CCCN=C=NCC.CCN(CC)CC.[Si](C#N)(C)(C)C.[C-]#N.[K+]>CC#N>[CH2:22]([O:21][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][NH:6][C:7]1[C:8]([CH3:20])=[C:9]([CH:13]=[CH:14][C:15]=1[S:16]([CH3:19])(=[O:18])=[O:17])[C:10]([C:26]1[CH:27]=[N:28][N:29]([CH2:30][CH3:32])[C:25]=1[OH:24])=[O:12])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 82115Trimethylsilyl cyanideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671984093-(2,2-Diethoxyethyl)amino-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178481816HCID 178481816, compound

Product

1
HCID 178467927HCID 178467927, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 0.38 g (1.1 mmol) of 3-(2,2-diethoxyethyl)amino-2-methyl-4-(methyl-sulfonyl)benzoic acid, 0.16 g (1.4 mmol) of 5-hydroxy-1-methylpyrazole and 0.25 g (1.3 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were dissolved in dry CH3CN. The mixture was stirred at RT for 1 day and allowed to stand for 2 days. 0.31 ml (2.2 mmol) of NEt3, 0.06 ml (0.4 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 removed and dried over MgSO4, and the solvent was removed under reduced pressure. The residue were purified by preparative HPLC. This gave 0.14 g of a red oil 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 removed
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe residue were purified by preparative HPLC

Sources & evidence

ORD record
ord-2fb5cf699f6f48d9a8e77637c8b45544
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