Hydrochloric Acid → 3-[(2-amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride

HRID 547562Notes

Reaction equation

HRID 547562 reaction equation
[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=2)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)=[O:14])[CH:6]=[C:5]([CH3:26])[N:4]=1.[Cl:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([N+:38]([O-:40])=[O:39])[CH:36]=2)[N:31]=[CH:30][CH:29]=1.Cl.CO.CCOC(C)=O>CCO.O.CCOC(C)=O>[ClH:27].[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=2)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[C:35]([N+:38]([O-:40])=[O:39])[CH:36]=4)[N:31]=[CH:30][CH:29]=3)=[CH:18][CH:17]=2)=[O:14])[CH:6]=[C:5]([CH3:26])[N:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2872104-Chloro-6-nitroquinolineHCID 21584119Ethylacetate methanolHCID 672024523-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide hydrochloride

Product 1

HCID 671998073-[(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 amine B3 (205 mg, 0.55 mmol) in EtOH (20 mL) and H2O (10 mL) was added 4-chloro-6-nitroquinoline (135 mg, 0.64 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 to give Cpd. RRR2 (217 mg 68%); m.p. (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ 13.00 (br, 2 H, 2×N+H), 10.99 (br, 1 H, NH), 10.75 (br s, 1 H, NH), 10.53 (s, 1 H, NH), 9.75 (d, J=1.9 Hz, 1 H, ArH), 8.64 (br d, J=7.4 Hz, 1 H, ArH), 8.60 (d, J=6.7 Hz, 1 H, ArH), 8.17 (d, J=9.3 Hz, 1 H, ArH), 8.15 (br, 1 H, NH), 8.07 (br s, 1 H, NH), 7.99 (d, J=8.8 Hz, 2 H, ArH), 7.79 (br d, J=7.5 Hz, 3 H, ArH), 7.57 (t, J=7.9 Hz, 1 H, ArH), 7.48 (d, J=8.8 Hz, 2 H, ArH), 6.91 (d, J=6.7 Hz, 1 H, ArH), 6.22 (d, J=0.6 Hz, 1 H, ArH), 2.30 (s, 3 H. CH3); HRMS (FAB+) calc. for C27H23N8O3 (M+1) m/z 507.1893, found 507.1888.

Workup

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

Sources & evidence

ORD record
ord-fb4a849b047346119d4bad3ec7215076
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

Loading…