Dicyclohexylamine → HCID 10983514, compound

HRID 1241707Notes

Reaction equation

HRID 1241707 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[N:16]([CH3:23])[C:15]4[C:10]=3[C:11]([CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=4)=[C:4]2[CH:3]=1.[CH2:32]([NH:35][C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])[CH:33]=[CH2:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(NC2CCCCC2)CCCCC1>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[N:16]([CH3:23])[C:15]4[C:10]=3[C:11]([CH:12]=[C:13](/[CH:34]=[CH:33]/[CH2:32][NH:35][C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])[CH:14]=4)=[C:4]2[CH:3]=1

Participants

8

Reactant 4

HCID 7582DicyclohexylamineHCID 11776TriphenylphosphineHCID 558569N-Allyl-2,2,2-trifluoroacetamideHCID 11016069HCID 11016069, compound2×

Product 1

HCID 10983514HCID 10983514, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(Method P) Under an atmosphere of nitrogen, trifluoromethanesulphonic acid 3-chloro-8-methyl-8H-quino[4,3,2-kl]acridin-6-yl ester, 38 (30 mg, 0.075 mmol), allyltrifluoroacetamide (17 mg, 1.5 eq), palladium (II) acetate (2 mg, 10 mol %), triphenyl phosphine (4 mg, 20 mol %), dicyclohexylamine (0.032 mL, 2 eq), and dioxane were mixed in a sealed tube and heated reflux in a sealed tube for 18 hrs. On cooling, the products were dissolved in dichloromethane and adsorbed onto silica. Separation of the more polar product by column chromatography (85:15 hexane:ethyl acetate) gave the title compound (22 mg, 0.045 mmol, 60%).

Workup

  1. temperatureheated
  2. temperaturereflux in a sealed tube for 18 hrs
  3. temperatureOn cooling
  4. customSeparation of the more polar product by column chromatography (85:15 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-7b1571f8a04047819d458c7d63e9b71d
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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