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

HRID 1711380Notes

Reaction equation

HRID 1711380 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:35]=[CH:36][CH:37]=2)[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=4)[N:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)=[O:13])[CH:5]=[C:4](C)[N:3]=1.[ClH:39].[NH2:40]C1N=C(NC2C=C(C=CC=2)C(NC2C=CC(N)=CC=2)=O)C=C(C)N=1.[Cl:65]C1C2C(=CC=C([N+]([O-])=O)C=2)N=CC=1.Cl>CCO.O.CCOC(C)=O.CO.CCOC(C)=O>[ClH:65].[ClH:39].[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:35]=[CH:36][CH:37]=2)[C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=4)[N:25]=[CH:24][CH:23]=3)=[CH:19][CH:20]=2)=[O:13])[CH:5]=[C:4]([NH2:40])[N:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 2872104-Chloro-6-nitroquinolineHCID 671998083-[(2-amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamideHCID 672024523-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide hydrochloride

Product 1

HCID 671994583-[(2,6-diamino-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
20 °C

Procedure

3-[(2-amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamide diihydrochloride (Cpd. RR2). 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. RR2 (217 mg 68%); m.p. (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ 13.00 (br, 2H, 2×N+H), 10.99 (br, 1H, NH), 10.75 (brs, 1H, NH), 10.53 (s, 1H, NH), 9.75 (d, J=1.9 Hz, 1 H, ArH), 8.64 (br d, J=7.4 Hz, 1H, ArH), 8.60 (d, J=6.7 Hz, 1H, ArH), 8.17 (d, J=9.3 Hz, 1H, ArH), 8.15 (br, 1H, NH), 8.07 (br s, 1H, NH), 7.99 (d, J=8.8 Hz, 2 H, ArH), 7.79 (br d, J=7.5 Hz, 3H, ArH), 7.57 (t, J=7.9 Hz, 1H, ArH), 7.48 (d, J=8.8 Hz, 2H, ArH), 6.91 (d, J=6.7 Hz, 1H, ArH), 6.22 (d, J=0.6 Hz, 1H, ArH), 2.30 (s, 3H. 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-f3eaaba434c349a8b3dd1e5cfcf10dd9
Source dataset
uspto-grants-2010_09
Patent number
US07790746B2

Reaction notes

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