Triethylamine → 1,1-Cyclopropanedicarboxamide

HRID 2060735Notes

Reaction equation

HRID 2060735 reaction equation
FC1C=CC([NH:8][C:9]([C:11]2([C:14](Cl)=[O:15])[CH2:13][CH2:12]2)=[O:10])=CC=1.C([N:19](CC)CC)C>C1COCC1>[C:11]1([C:14]([NH2:19])=[O:15])([C:9]([NH2:8])=[O:10])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 580832671-[(4-Fluorophenyl)carbamoyl]cyclopropanecarbonyl chloride

Product 1

HCID 2992011,1-CyclopropanedicarboxamideYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-((4-fluorophenyl)carbamoyl)cyclopropanecarbonyl chloride prepared via the procedure in Example 47 (0.13 g, 0.538 mmol), Example A9 (0.123 g, 0.414 mmol), and triethylamine (0.065 ml, 0.621 mmol) were dissolved in THF (3 ml). The mixture was stirred at RT for 30 min, filtered to remove triethylamine HCl, concentrated under reduced pressure and purified by silica gel column chromatography (MeOH/DCM) to obtain N-(2-fluoro-5-methyl-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-N′-4-fluorophenyl)cyclopropane-1,1-dicarboxamide (0.067 g, 32% yield). MS (ESI) m/z: 504.2 (M+H+).

Workup

  1. filtrationfiltered
  2. customto remove triethylamine HCl
  3. concentrationconcentrated under reduced pressure
  4. custompurified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-dc2f3173299e4d718e7fcb0695ef2631
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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