Hydrochloric Acid → 4-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-[4-(4-quinolinylamino)phenyl]benzamide dihydrochloride

HRID 1711366Notes

Reaction equation

HRID 1711366 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]=[CH:34][CH:35]=2)[N:30]=[CH:29][CH:28]=1.[ClH:37].CO.CCOC(C)=O>CCO.O.CCOC(C)=O>[ClH:26].[ClH:37].[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]=[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 691404-ChloroquinolineHCID 21584119Ethylacetate methanolHCID 672005514-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide

Product 1

HCID 671984804-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-[4-(4-quinolinylamino)phenyl]benzamide dihydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of C3 (218 mg, 0.54 mmol) in EtOH (20 mL) and H2O (10 mL) was added 4-chloroquinoline (96 mg, 0.59 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. GG1 (259 mg 98%) as a yellow solid.; M.P (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ13.75 (br. 2 H, 2×N+H), 11.07 (s, 1H, NH), 10.99 (s, 1H, NH), 10.52 (s, 1H, NH), 8.83 (d, J=8.4 Hz, 1H, ArH), 8.50 (d, J=7.0 Hz, 1H, ArH), 8.11-7.99 (m, 10H, ArH & NH2), 7.80 (dt, J=8.0, 1.1 Hz, 1H, ArH), 7.48 (d, J=8.9 Hz, 2H, ArH), 6, 78 (d, J=7.0 Hz, 1H, ArH), 6.35 (s, 1H, ArH), 2.31 (s, 3H, CH3); 13C NMR [(CD3)2SO] δ 164.8, 161.6, 155.9, 155.0, 153.3, 142.5, 141.4, 138.4, 138.1, 133.7, 132.1, 129.6, 128.5 (2×C), 126.8, 125.8 (2×C), 123.5, 121.4 (2×C), 120.2, 120.1, 116.9, 99.6, 94.3, 18.4, one of the quaternary carbons were difficult to observe; HRMS FAB+ calc. for C27H25N7O (M+1) m/z, 462.2042 found 462.2047.

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-e2d59acb77de4d7e8b50a8f00b5519f9
Source dataset
uspto-grants-2010_09
Patent number
US07790746B2

Reaction notes

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