Triethylamine → 2-(4-(8-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

HRID 476162Notes

Reaction equation

HRID 476162 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[C:20]#[N:21])=[CH:15][CH:14]=1)=[CH:9][C:8]([CH3:24])=[CH:7][CH:6]=2.C(N(CC)CC)C.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH3:23][C:19]([C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:11]3[C:10]4[CH:9]=[C:8]([CH3:24])[CH:7]=[CH:6][C:5]=4[N:4]=[CH:3][C:2]=3[NH:1][C:33]2=[O:35])=[CH:14][CH:15]=1)([CH3:22])[C:20]#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 668804232-(4-(3-Amino-6-methyl-quinolin-4-ylamino)phenyl)-2-methylpropanenitrile

Product 1

HCID 668966092-(4-(8-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-(3-amino-6-methyl-quinolin-4-ylamino)phenyl)-2-methylpropanenitrile (Compound of Preparation J, 190 mg, 0.6025 mmol) and triethylamine (0.12 ml, 0.901 mmol) in CH2Cl2 (10 mL) was added over 40 min to a solution of triphosgene (195 mg, 0.6139 mmol) in 5 mL of CH2Cl2 at 0° C. The reaction mixture was stirred for 20 min at this temperature then was quenched with saturated aqueous NaHCO3, stirred for 5 min and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and evaporated in vacuo to obtain the title compound as brown solid. Yield: 145 mg (70%); 1H NMR (DMSO-d6, 300 MHz): δ 11.641 (s, 1H), 8.678 (s, 1H), 7.864-7.892 (d, 1H, J=8.4 Hz), 7.782-7.810 (d, 2H, J=8.4 Hz), 7.629-7.657 (d, 2H, J=8.4 Hz), 7.342-7.371 (d, 1H, J=8.7 Hz), 6.625 (s, 1H), 2.147 (s, 3H), 1.801 (s, 6H); MS: m/z 343 (M+).

Workup

  1. customthen was quenched with saturated aqueous NaHCO3
  2. stirringstirred for 5 min
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-3b7072e445344b5b82addbd15cc36e0c
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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