Hydrochloric Acid → HCID 67198444, compound

HRID 547555Notes

Reaction equation

HRID 547555 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]3[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([NH2:23])[N:17]=3)[CH:10]=2)=[O:7])=[CH:4][CH:3]=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].[NH2:23][C:18]1[N:17]=[C:16]([NH:15][C:11]2[CH:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:24]=[CH:25][C:2]([NH:1][C:30]4[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=[CH:32][CH:31]=4)=[CH:3][CH:4]=3)[CH:14]=[CH:13][CH:12]=2)[CH:21]=[C:20]([CH3:22])[N:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 691404-ChloroquinolineHCID 67202049HCID 67202049, compound

Product 1

HCID 67198444HCID 67198444, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of amine E4 (0.26 g, 0.63 mmol) in 1:2 EtOH:H2O (30 mL) were sequentially added 4-chloroquinoline (0.62 g, 3.78 mmol) and c.HCl (0.17 mL, 5.67 mmol), and the resulting mixture refluxed for 3 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=0.43, yellow spot after staining with KMnO4). After this time, solvent was removed under reduced pressure, and the residue dried via three MeOH-azeotrope cycles. The residue was re-precipitated from MeOH:EtOAc to give Cpd. II as an amorphous lemon-yellow solid (0.27 g, 79%); mp 251-255° C. (powder-glue); 1H NMR (400 MHz, DMSO): δ 14.78 (v br s, 1H, quinolinyl-N+—H), 12.79 (v br s, 1H, pyrimidinyl-N+—H), 11.14 (s, 1H, ArNHAr), 10.64 (br s, 1H, ArC(O)NHAr), 10.52 (s, 1H, ArNHAr), 8.87 (d, J=8.44 Hz, 1H, ArH), 8.61 (d, J=6.94 Hz, 1H, ArH), 8.30-7.45 (m, 12H, ArH & ArNH2), 7.38 (t, J=8.07 Hz, 1H, ArH), 7.00 (d, J=6.94 Hz, 1H, ArH), 6.22 (s, 1H ArH), 2.29 (s, 3H, ArCH3); LCMS (APCI+): 463 (100%); HPLC: 95.4%.

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 three MeOH-azeotrope cycles
  5. customThe residue was re-precipitated from MeOH
  6. customEtOAc to give Cpd

Sources & evidence

ORD record
ord-8efbb27959674db3a7960b601cb24bce
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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