Triethylamine → HCID 68808743, compound

HRID 2217902Notes

Reaction equation

HRID 2217902 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5]C(=O)OC(C)(C)C)[CH2:2]1.Cl[C:14]1[CH:23]=[CH:22][C:21]2[C:20]([C:24]([NH:26][CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:25])=[C:19]([Cl:34])[CH:18]=[CH:17][C:16]=2[N:15]=1.C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[NH3:1].[NH2:5][CH:3]1[CH2:2][N:1]([C:14]2[CH:23]=[CH:22][C:21]3[C:20]([C:24]([NH:26][CH2:27][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]4)=[O:25])=[C:19]([Cl:34])[CH:18]=[CH:17][C:16]=3[N:15]=2)[CH2:4]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 860130222,6-dichloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide

Product 2

HCID 222AmmoniaYield 10%HCID 68808743HCID 68808743, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

3-Azetidinyl-carbamic acid, 1,1-dimethylethyl ester (0.5 g) was added to 2,6-dichloro-N-(cyclohexylmethyl)quinoline-5-carboxamide (Example 43(a)) (0.28 g), tetra-butylammonium bromide (0.28 g) and triethylamine (0.5 mL) in acetonitrile (4 mL). The reaction mixture was heated at 120° C. in a microwave for 1 hour, concentrated under reduced pressure and purified (SiO2, methanol:dichloromethane 4:96 as eluant). The residue (0.24 g) was dissolved in dichloromethane and trifluoroacetic acid (1 mL) added. The reaction mixture was stirred at room temperature for 1 hour, concentrated and then treated with 7M ammonia in methanol. Purification (Varian SCX cartridge using methanol and then 10% ammonia in methanol) gave the sub-titled compound as a solid (0.1 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified (SiO2, methanol:dichloromethane 4:96 as eluant)
  3. dissolutionThe residue (0.24 g) was dissolved in dichloromethane
  4. additiontrifluoroacetic acid (1 mL) added
  5. concentrationconcentrated
  6. additiontreated with 7M ammonia in methanol
  7. customPurification (Varian SCX cartridge

Sources & evidence

ORD record
ord-8ef91228a2204ca2b3a417b5af282208
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

Loading…