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

HRID 547561Notes

Reaction equation

HRID 547561 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18]3[CH:23]=[C:22]([NH2:24])[N:21]=[C:20]([NH2:25])[N:19]=3)[CH:12]=2)=[CH:5][CH: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].[NH2:25][C:20]1[N:19]=[C:18]([NH:17][C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([NH:2][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:4][CH:5]=2)=[O:26])[CH:23]=[C:22]([NH2:24])[N:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2872104-Chloro-6-nitroquinolineHCID 21584119Ethylacetate methanolHCID 67200187N-(4-Aminophenyl)-3-[(2,6-diamino-4-pyrimidinyl)amino]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 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of amine B6 (204 mg, 0.55 mmol) in EtOH (20 mL) and H2O (10 mL) was added 4-chloro-6-nitroquinoline (126 mg, 0.61 mmol) and stirred until it dissolved, then 2 drops of c.HCl was added. The reaction mixture was refluxed for 4 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. RRR1 (224 mg 70%); m.p. (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ 14.75 (br, 1 H, N+H), 11.50 (br, 1 H, N+H), 11.10 (br, 1 H, NH), 10.50 (s, 1 H, NH), 9.88 (s, 1 H, NH), 9.77 (s, 1 H, NH), 9.76 (s, 1 H, ArH), 8.66 (d, J=9.3 Hz, 1 H, ArH), 8.60 (d, J=6.8 Hz, 1 H, ArH), 8.19 (d, J=9.3 Hz, 1 H, ArH), 8.25 (d, J=8.8 Hz, 2 H, ArH), 7.94 (br s 2 H, NH2), 7.71 (d, J=7.6 Hz, 1 H, ArH), 7.56-7.42 (m, 6 H, NH2 & 4×ArH), 6.91 (d, J=6.8 Hz, 1 H, ArH), 5.44 (s, 1 H, ArH). HRMS (FAB+) calc. for C26H22N9O3 (M+1) m/z 508.1846, found 508.1841.

Workup

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

Sources & evidence

ORD record
ord-f7a138fa76154632945551b8fcebd98b
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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