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Triethylamine → HCID 178480295, compound

HRID 1931120
Notes
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Reaction equation

HRID 1931120 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:15][CH2:14][CH2:13]2)[C:7](=[NH:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:26]=[CH:25][C:24]([S:27](=[O:30])(=[O:29])[NH2:28])=[CH:23][C:19]=1[C:20](O)=[O:21].CCN(CC)CC.C(P(=O)(OCC)OCC)#N>C1COCC1>[NH2:28][S:27]([C:24]1[CH:25]=[CH:26][C:18]([F:17])=[C:19]([CH:23]=1)[C:20](/[N:16]=[C:7]1/[N:8]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15]2)[N:9]([CH3:10])[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6]/1)=[O:21])(=[O:30])=[O:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 24926842-Fluoro-5-sulfamoylbenzoic acidHCID 666432695-Tert-butyl-2-(cyclobutylmethyl)-1-methyl-1h-pyrazol-3(2h)-imine

Product 1

HCID 178480295HCID 178480295, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of Example 113C (0.43 g, 1.9 mmol) and 2-fluoro-5-sulfamoylbenzoic acid (Enamine, 0.47 g, 2.1 mmol) in THF (10 mL) was added Et3N (0.68 mL, 4.9 mmol) followed by diethyl cyanophosphonate (0.44 mL, 2.9 mmol). The mixture was stirred at ambient temperature for 2 hours then concentrated under reduced pressure. Purification by column chromatography (SiO2, 50% hexanes/EtOAc to 100% EtOAc to 9:1:0.1 EtOAc:MeOH:Et3N) afforded the title compound (0.26 g, 0.62 mmol, 32% yield). MS (DCI/NH3) m/z 423 (M+H)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customPurification by column chromatography (SiO2, 50% hexanes/EtOAc to 100% EtOAc to 9:1:0.1 EtOAc:MeOH:Et3N)

Sources & evidence

ORD record
ord-e64fca9a93e942c49d5d797788a42009
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188135B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes