4-Methoxybenzylamine → 2-{4-[4-(4-Methoxy-benzylamino)-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-phenyl}-2-methyl-propionitrile

HRID 1971237Notes

Reaction equation

HRID 1971237 reaction equation
Cl[C:2]1[C:11]2[N:12]([CH3:27])[C:13](=[O:26])[N:14]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=3)[C:10]=2[C:9]2[CH:8]=[C:7]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:6]=[CH:5][C:4]=2[N:3]=1.C([O-])(C)(C)C.[Na+].[CH3:44][O:45][C:46]1[CH:53]=[CH:52][C:49]([CH2:50][NH2:51])=[CH:48][CH:47]=1>CN(C1C(C2[C-]=CC=CC=2)=CC=CC=1)C.C1[C@H]2CC(PC3[C@H]4C[C@H](CC4)C3)[C@H](C2)C1.Cl[Pd+].C1(C)C=CC=CC=1>[CH3:44][O:45][C:46]1[CH:53]=[CH:52][C:49]([CH2:50][NH:51][C:2]2[C:11]3[N:12]([CH3:27])[C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:10]=3[C:9]3[CH:8]=[C:7]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:6]=[CH:5][C:4]=3[N:3]=2)=[CH:48][CH:47]=1

Participants

6

Reactant 3

HCID 754524-MethoxybenzylamineHCID 23676156Sodium t-butoxideHCID 536303582-[4-(4-Chloro-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile

Product 1

HCID 536303572-{4-[4-(4-Methoxy-benzylamino)-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-phenyl}-2-methyl-propionitrile

Reagents, catalysts & solvents 2

HCID 11272965[(1R,4S)-2-Bicyclo[2.2.1]heptanyl]-[(1S,4R)-2-bicyclo[2.2.1]heptanyl]phosphane;chloropalladium(1+);N,N-dimethyl-2-phenylanilineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

100 mg (0.198 mmol) of 2-[4-(4-chloro-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile (Example 109b), 27 mg (0.278 mmol) sodium tert-butanolate, 11 mg (0.02 mmol) SK-CC01-A catalyst and 33 mg (0.238 mmol) 4-methoxybenzylamine in 0.4 ml degassed toluene under argon are heated at 100° C. for 22 h. The reaction mixture is quenched with sat. aqueous NaHCO3 and extracted with CH2Cl2 (2×). The organic layers are washed with sat. aqueous NaHCO3, dried over Na2SO4, filtered and evaporated to provide the title compound as a crude brown solid. ES-MS: 605 (M+H)+; analytical HPLC: tret=3.29 minutes (Grad 1).

Workup

  1. customThe reaction mixture is quenched with sat. aqueous NaHCO3
  2. extractionextracted with CH2Cl2 (2×)
  3. washThe organic layers are washed with sat. aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ccb2058bba0d498c889ba80d45a7f620
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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