Triethylamine → 2-Amino-N-bicyclopropyl-1-yl-5-cyano-3-methyl-benzamide

HRID 1819278Notes

Reaction equation

HRID 1819278 reaction equation
[CH3:1][C:2]1[C:7]2[NH:8]C(=O)O[C:11](=[O:12])[C:6]=2[CH:5]=[C:4]([C:14]#[N:15])[CH:3]=1.Cl.[C:17]1([NH2:23])([CH:20]2[CH2:22][CH2:21]2)[CH2:19][CH2:18]1.C(N(CC)CC)C>C1COCC1>[NH2:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([C:14]#[N:15])=[CH:5][C:6]=1[C:11]([NH:23][C:17]1([CH:20]2[CH2:22][CH2:21]2)[CH2:19][CH2:18]1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53433499(1,1'-Bi(cyclopropan))-1-amine hydrochlorideHCID 578871986-cyano-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 578872112-Amino-N-bicyclopropyl-1-yl-5-cyano-3-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

236 mg (1.16 mmol) 8-methyl-2,4-dioxo-1,4-dihydro-2H-benzo[d][1,3]oxazine-6-carbonitrile, 234 mg (1.75 mmol) bicyclopropyl-1-ylamine hydrochloride and 177 mg (1.75 mmol) triethylamine in 25 ml THF are heated 4 h at reflux. The mixture is cooled down and evaporated. The residue is dissolved in ethyl acetate and extracted with water. After purification on a short path of silicagel, 63 mg of the title compound are isolated as yellow crystals. F: 171-172° C.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture is cooled down
  3. customevaporated
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. extractionextracted with water
  6. customAfter purification on a short path of silicagel, 63 mg of the title compound
  7. customare isolated as yellow crystals
  8. custom171-172° C.

Sources & evidence

ORD record
ord-5e794d64a1cf4c6bb2a273a89314e5f0
Source dataset
uspto-grants-2009_10
Patent number
US07601743B2

Reaction notes

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