Hydrochloric Acid → 4-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride

HRID 547548Notes

Reaction equation

HRID 547548 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[O:14])=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:25])[N:3]=1.[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([N+:37]([O-:39])=[O:38])[CH:35]=2)[N:30]=[CH:29][CH:28]=1.[ClH:40].CO.CCOC(C)=O>CCO.O.CCOC(C)=O>[ClH:26].[ClH:40].[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:27]4[C:36]5[C:31](=[CH:32][CH:33]=[C:34]([N+:37]([O-:39])=[O:38])[CH:35]=5)[N:30]=[CH:29][CH:28]=4)=[CH:18][CH:17]=3)=[O:14])=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:25])[N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2872104-Chloro-6-nitroquinolineHCID 21584119Ethylacetate methanolHCID 672005514-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide

Product 1

HCID 672007844-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of compound C3 (200 mg, 0.49 mmol) in EtOH (20 mL) and H2O (10 mL) was added 4-chloro-6-nitroquinoline (113 mg, 0.54 mmol) and stirred until it dissolved, then 2 drops of c.HCl was added. The reaction mixture was refluxed for 3 h., diluted with EtOAc, brought to boil and cool to 20° C. The resulting precipitate was filtered and recrystallized from MeOH/EtOAc/Charcoal/Celite to give Cpd. GG4 (247 mg 87%) as a yellow solid.; M.P (MeOH/EtOAc) 295-300° C.; 1H NMR [(CD3)2SO] δ13.50 (br, 2 H, 2×N+H), 11.32 (br, 1 H, NH), 11.00 (brs, 1 H, NH), 10.51 (s, 1 H, NH), 9.81 (d, J=2.2 Hz, 1 H, ArH), 8.69 (dd, J=9.3, 2.2 Hz, 1 H, ArH), 8.59 (d, J=6.9 Hz, 1 H, ArH), 8.24 (d, J=9.3 Hz, 1 H, ArH), 8.06-7.98 (m, 7H, ArH & NH2), 7.48 (d, J=8.9 Hz, 2 H, ArH), 6.90 (d, J=6.9 Hz, 1 H, ArH), 6.32 (s, 1 H, ArH), 2.32 (d, J=0.4 Hz, 3 H, CH3); HRMS (FAB+) calc. for C27H23N8O3 (M+) m/z 507.1893, found 507.1896.

Workup

  1. dissolutiondissolved
  2. temperatureThe reaction mixture was refluxed for 3 h.
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized from MeOH/EtOAc/Charcoal/Celite
  5. customto give Cpd

Sources & evidence

ORD record
ord-14ef1edb8da54270b9738674b1beb09b
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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