Hydrochloric Acid → N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(7-(dimethylamino)quinolin-4-ylamino)benzamide hydrochloride

HRID 547537Notes

Reaction equation

HRID 547537 reaction equation
Cl.[NH2:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=3)=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1.CCO.Cl.[Cl:31][C:32]1[C:41]2[C:36](=[CH:37][C:38]([N:42]([CH3:44])[CH3:43])=[CH:39][CH:40]=2)[N:35]=[CH:34][CH:33]=1>CC(O)=O.O.CCCCO>[ClH:31].[NH2:24][C:19]1[N:18]=[C:17]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:25]=[CH:26][C:3]([NH:2][C:32]4[C:41]5[C:36](=[CH:37][C:38]([N:42]([CH3:44])[CH3:43])=[CH:39][CH:40]=5)[N:35]=[CH:34][CH:33]=4)=[CH:4][CH:5]=3)=[CH:15][CH:14]=2)[CH:22]=[C:21]([CH3:23])[N:20]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3336214-chloro-N,N-dimethylquinolin-7-amineHCID 672000444-Amino-N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]benzamide hydrochloride2×

Product 1

HCID 24860001N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(7-(dimethylamino)quinolin-4-ylamino)benzamide hydrochloride

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 2631-ButanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of amide E5 (306 mg, 0.83 mmol) in 1:2 EtOH:H2O (10 mL) were sequentially added c.HCl (0.23 mL) and 4-chloro-7-dimethylamino-quinoline (Z1) (188 mg, 0.91 mmol), and the resulting mixture was refluxed for 20 h. After this time [when MS and TLC analysis (5:4:1 n-BuOH:H2O:CH3CO2H) of the reaction mixture suggested the remaining small quantity of E5 was degrading], the reaction mixture was filtered, and the resulting solid washed sequentially with EtOAc and hexanes, to furnish Cpd. BB as an amorphous lemon-yellow solid (199 mg, 45%). 1H NMR [CD3)2SO]: 2.28 [s, 3H, ArCH3], 3.15 [s, 6H, ArN(CH3)2], 6.18 [br s, 1H, ArH], 6.70 [d, J=7.02 Hz, 1H, ArH], 6.88 [d, J=2.46 Hz, 1H, ArH], 7.38 [dd, J=9.62, 2.46 Hz, 1H, ArH], 7.61 [d, J=8.60, 2H, ArH], 7.81 [m, 5H, ArH & ArNH2], 8.14 [d, J=8.60 Hz, 2H, ArH], 8.31 [d, J=7.02 Hz, 1H, ArH], 8.55 [d, J=9.71 Hz, 1H, ArH], 10.41 [br s, 1H, ArH], 10.65 [m, 2H, ArNHAr & ArNHAr], 12.68 [v br s, 1H, ArC(O)NH], 13.77 [v br s, 1H, quinolinyl N+H]. LCMS (APCI+): 506 (100%). HPLC: 96.6%.

Workup

  1. filtrationwas filtered
  2. washthe resulting solid washed sequentially with EtOAc and hexanes
  3. customto furnish Cpd

Sources & evidence

ORD record
ord-f448ae8c6f364983956528fae906eb31
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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