Hydrochloric Acid → 3-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-[4-(4-quinolinylamino)phenyl]benzamide dihydrochloride

HRID 1711362Notes

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]=[CH:35][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]=[CH:35][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

Conditions

Temperature: 20 °C

Procedure

To a solution of compound B3 (150 mg, 0.37 mmol) in EtOH (15 mL) and H2O (7.5 mL) was added 4-chloroquinoline (73 mg, 0.45 mmol) and stirred until it dissolved, then 2 drops of c. HCl was added. The reaction mixture was refluxed for 20 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. FF1 (195 mg, 96%) as a yellow solid.; M.P (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ 13.72 (v br, 2H, 2×N+H), 10.91 (brs, 1H, NH), 10.96 (brs, 1H, NH), 10.56 (s, 1H, HN), 8.79 (d, J=8.5 Hz, 1H, ArH), 7.50 (d, J=6.9 Hz, 1H, ArH), 8.14-7.99 (m, 6 H, ArH & NH2), 7.83 (m, 3H, ArH), 7.55 (t, J=7.9 Hz, 1H, ArH), 7.49 (d, J=8.8 Hz, 2H, ArH), 6.78 (d, J=6.9 Hz, 1H, ArH), 6.24 (s, 1H, ArH), 2.30 (s, 3H, ArH), mass APCl+476.

Workup

dissolutiondissolved
temperatureThe reaction mixture was refluxed for 20 h
filtrationThe resulting precipitate was filtered
customrecrystallized from MeOH/EtOAc/Charcoal/Celite
customto give Cpd

Sources & evidence

ORD record: ord-3361718881f3408e997a7a1e66f9c235
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790746B2

Reaction notes

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