Diisopropylethylamine → 6-((11-Hydroxyundecyl)thio)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

HRID 1944885Notes

Reaction equation

HRID 1944885 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][C:6]([C:13]([NH2:15])=[O:14])=[C:5]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1.CCN(C(C)C)C(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[SH:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][OH:88]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[OH:88][CH2:87][CH2:86][CH2:85][CH2:84][CH2:83][CH2:82][CH2:81][CH2:80][CH2:79][CH2:78][CH2:77][S:76][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][C:6]([C:13]([NH2:15])=[O:14])=[C:5]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 26182411-MercaptoundecanolHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 575169476-Iodo-4-(3-methoxyphenylamino)-8-methylquinoline-3-carboxamide

Product 1

HCID 585051446-((11-Hydroxyundecyl)thio)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was synthesized in a manner analogous to that described in Org. Lett. 2004, 6(24), 4587-4590. To a round bottom flask were added 6-iodo-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide (1.0 g, 2.31 mmol), dry dioxane (23 mL) and i-Pr2NEt (0.81 mL, 4.62 mmol). Catalytic Pd2(dba)3 (63 mg, 0.07 mmol), Xantphos (80 mg, 0.14 mmol) and 11-mercapto-1-undecanol (494 mg, 2.42 mmol) were then added. The mixture was evacuated and backfilled with nitrogen (3 cycles). The mixture was heated to reflux for 2 h (HPLC confirmed the completion of the reaction). The reaction mixture was then allowed to reach ambient temperature followed by filtration and concentration. The crude product was used without further purification for the next step. ES/MS calcd. for C29H40N3O3S+ 510.3. Found m/z=510.4 (M+H)+.

Workup

  1. customThe mixture was evacuated
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 2 h (HPLC
  4. customthe completion of the reaction)
  5. customto reach ambient temperature
  6. filtrationfollowed by filtration and concentration
  7. customThe crude product was used without further purification for the next step

Sources & evidence

ORD record
ord-7c49e4b130e34235918db9a4dc0d39cc
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

Loading…