Hydrochloric Acid → 4-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(7-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride

HRID 1711368Notes

Reaction equation

HRID 1711368 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][C:33]([N+:37]([O-:39])=[O:38])=[CH:34][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][C:33]([N+:37]([O-:39])=[O:38])=[CH:34][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 123225804-Chloro-7-nitroquinolineHCID 21584119Ethylacetate methanolHCID 672005514-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide

Product 1

HCID 672014394-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(7-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 C3 (235 mg, 0.58 mmol) in EtOH (20 mL) and H2O (10 mL) was added 4-chloro-7-nitroquinoline (132 mg, 0.63 mmol) and stirred until it dissolved, then 2 drops of c.HCl was added. The reaction mixture was refluxed for 5 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. GG5 (317 mg 94%) as a yellow solid.; m.p (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ 12.9 (br, 1 H, N+H), 10.81 (brs, 2H, 2×NH), 10.44 (s, 1H, NH), 8.93 (d, J=9.3 Hz, 1H, ArH), 8.81 (d, J=1.9 Hz, 1H, ArH), 8.66 (d, J=6.6 Hz, 1H, ArH), 8.46 (d, J=8.9 Hz, 1 H, ArH), 8.05-7.98 (m, 8H, ArH & NH2), 7.47 (d, J=8.8 Hz, 1H, ArH), 6.94 (d, J=6.6 Hz, 1H, ArH), 6.26 (s, 1H, ArH), 2.32 (s, 3H, CH3); HRMS (FAB+) calc. for C27H23N8O3 (M+1) m/z 507.1893, found 507.1885.

Workup

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

Sources & evidence

ORD record
ord-9888d40cf0724a44afb8646aee4c6a23
Source dataset
uspto-grants-2010_09
Patent number
US07790746B2

Reaction notes

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