Methylamine → N-Cycloheptyl-N-methyl-[2,1,3]-benzoxadiazole-5-carboxamide

HRID 238535Notes

Reaction equation

HRID 238535 reaction equation
[C:1]1(=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN.[CH2:11]([N:13](CC)CC)C.[N:18]1[O:19][N:20]=[C:21]2[CH:26]=[C:25]([C:27](Cl)=[O:28])[CH:24]=[CH:23][C:22]=12>C(O)C.ClCCl.[Pd].CCOCC>[CH:1]1([N:13]([CH3:11])[C:27]([C:25]2[CH:24]=[CH:23][C:22]3=[N:18][O:19][N:20]=[C:21]3[CH:26]=2)=[O:28])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 10400CycloheptanoneHCID 27354532,1,3-Benzoxadiazole-5-carbonyl chloride

Product 1

HCID 25103927N-Cycloheptyl-N-methyl-[2,1,3]-benzoxadiazole-5-carboxamide

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cycloheptanone (1.12 g, 10 mmol) in 40 ml of ethanol was added a methylamine (2.5 ml of a 33% solution in ethanol) and 220 mg of Pd on C (10%) were added, and the mixture hydrogenated at 50 psi over night. The solids were filtered off and the mixture concentrated under vacuum to give a pale yellow oil. This material and 1.2 ml of triethylamine were dissolved in 10 ml of dichloromethane and a solution of [2,1,3]-benzoxadiazole-5-carbonylchloride (730 mg, 4 mmol) was added slowly. After stirring the mixture for 2 hours, the organic phase was washed with 1N HCl and cone. NaHCO3 solution, dried over magnesium sulfate, and then concentrated under vacuum to give a white solid, after trituration with ether (405 mg, 37%). Mp: 80-81° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.93 (m, 1H); 7.80 (s, 1H); 7.43-7.37 (m, 1H); 4.75-4.60 and 3.70-3.55 (m+m, 1H); 3.01 and 2.87 (s+s, 3H); 2.00-1.20 ppm (m, 12H).

Workup

  1. additionwere added
  2. waitthe mixture hydrogenated at 50 psi over night
  3. filtrationThe solids were filtered off
  4. concentrationthe mixture concentrated under vacuum
  5. customto give a pale yellow oil
  6. washthe organic phase was washed with 1N HCl and cone
  7. dry with materialNaHCO3 solution, dried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customto give a white solid

Sources & evidence

ORD record
ord-ae74bf8ab08f4ace9edff99c6e4b4f70
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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