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

HRID 1711377Notes

Reaction equation

HRID 1711377 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.[Cl:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=[CH:32][CH:31]=1.Cl>O>[ClH:29].[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:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=[CH:32][CH:31]=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 691404-ChloroquinolineHCID 873068154-amino-N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]benzamide;dihydrochloride

Product 1

HCID 87307497N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]-4-(quinolin-4-ylamino)benzamide;dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of triamine F5 (0.35 g, 0.91 mmol) in 1:2 EtOH:H2O (30 mL) were sequentially added 4-chloroquinoline (0.64 g, 3.90 mmol) and c.HCl (0.25 mL, 8.24 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; product Rf=0.51, yellow spot after staining with KMnO4). 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. JJ2 (91 mg, 20%) as a pale yellow amorphous solid; mp 240-244° C. (powder→glue), 264-268° C. (glue→liquid); 1H NMR (400 MHz, DMSO): δ 14.67 (br s, 1H, quinolinyl-N30—H), 11.19 (s, 1H, hydrazonyl-N30—H), 11.07 (s, 1H, ArC(O)NHAr), 10.48 (s, 1H, ArNHAr), 8.72 (d, J=8.52 Hz, 1H, ArH), 8.61 (d, J=6.90 Hz, 1H, ArH), 8.24 (m, 3H, ArH), 8.08 (m, 2H, ArH), 7.95 (d, J=8.10 Hz, 1H, ArH), 7.82 (m, 6H, ArH & ═C(NH2)2), 7.68 (d, J=8.38 Hz, 2H, ArH), 7.43 (t, J=7.97 Hz, 1H, ArH), 7.01 (d, J=6.90 Hz, 1H, ArH), 2.37 (s, 3H, Ar(CH3)2═N—); LCMS (APCl+): 438 (100%); HPLC: 96.4%.

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 240-244° C. (powder→glue), 264-268° C. (glue→liquid)

Sources & evidence

ORD record
ord-70d0e3bbd44c410db8cc5123718b7fe2
Source dataset
uspto-grants-2010_09
Patent number
US07790746B2

Reaction notes

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