Hydrochloric Acid → N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]-4-[[6-(dimethylamino)quinolin-4-yl]amino]benzamide;dihydrochloride

HRID 547557Notes

Reaction equation

HRID 547557 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:25]=[CH:24][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13](/[C:17](=[N:19]/[N:20]=[C:21]([NH2:23])[NH2:22])/[CH3:18])[CH:12]=2)=[O:9])=[CH:6][CH:5]=1.CCO.[CH3:29][N:30]([CH3:42])[C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[CH:36][CH:35]=[C:34]2[Cl:41].Cl>O>[ClH:41].[ClH:1].[NH2:22][C:21](=[N:20]/[N:19]=[C:17](/[C:13]1[CH:12]=[C:11]([NH:10][C:8](=[O:9])[C:7]2[CH:6]=[CH:5][C:4]([NH:3][C:34]3[C:33]4[C:38](=[CH:39][CH:40]=[C:31]([N:30]([CH3:42])[CH3:29])[CH:32]=4)[N:37]=[CH:36][CH:35]=3)=[CH:25][CH:24]=2)[CH:16]=[CH:15][CH:14]=1)\[CH3:18])[NH2:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 436172264-chloro-N,N-dimethylquinolin-6-amineHCID 873068154-amino-N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]benzamide;dihydrochloride

Product 1

HCID 87306434N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]-4-[[6-(dimethylamino)quinolin-4-yl]amino]benzamide;dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of triamine F5 (0.22 g, 0.59 mmol) in 1:2 EtOH:H2O (60 mL) were sequentially added 6-dimethylamino-4-chloroquinoline (0.13 g, 0.64 mmol) and c.HCl (0.16 mL, 5.32 mmol), and the resulting solution was refluxed for 20 h (reaction progress followed by TLC, eluting with the top phase of a 5:4:1 mixture of n-BuOH:H2O:acetic acid). After this time, solvent was removed under reduced pressure, and the residue dried via two MeOH-azeotrope cycles. The residue was re-precipitated from MeOH:EtOAc to give Cpd. JJ1 (61 mg, 19%) as an amorphous dark brown solid; mp 239-243° C. (powder-glue), 278-282° C. (glue-liquid); 1H NMR (400 MHz, DMSO): δ 14.44 (s, 1H, quinolinyl-N+—H), 11.20 (s, 1H, hydrazonyl-N+—H), 10.58 (s, 1H, ArC(O)NHAr), 10.46 (s, 1H, ArNHAr), 8.35 (d, J=6.71 Hz, 1H, ArH), 8.26 (t, J=1.73 Hz, 1H, ArH), 8.22 (d, J=8.61 Hz, 3H, ArH), 7.95 (m, 2H, ArH), 7.79 (m, 5H, ArH & ═C(NH2)2), 7.69 (d, J=2.52 Hz, 1H, ArH), 7.66 (d, J=8.61 Hz, 2H, ArH), 7.58 (d, J=2.43 Hz, 1H, ArH), 7.43 (t, J=7.98 Hz, 1H, ArH), 6.95 (d, J=6.71 Hz, 1H, ArH), 3.15 (s, 6H, ArN(CH3)2), 2.37 (s, 3H, Ar(CH3)═N—); LCMS (APCI+): 482 (100%); HPLC: 95.8%.

Workup

  1. customreaction progress
  2. washeluting with the top phase of a 5:4:1 mixture of n-BuOH
  3. customAfter this time, solvent was removed under reduced pressure
  4. dry with materialthe residue dried via two MeOH-azeotrope cycles
  5. customThe residue was re-precipitated from MeOH
  6. customEtOAc to give Cpd
  7. custommp 239-243° C. (powder-glue), 278-282° C. (glue-liquid)

Sources & evidence

ORD record
ord-61d720627397495cba1249e05a345d3a
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

Loading…