Hydrochloric Acid → HCID 67202049, compound

HRID 547554Notes

Reaction equation

HRID 547554 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:26])[C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[CH:12]=[CH:13][CH:14]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1.CCO.Cl>[Fe].O>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]3[CH:5]=[C:4]([CH3:27])[N:3]=[C:2]([NH2:1])[N:7]=3)[CH:10]=2)=[O:26])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67198596HCID 67198596, compound

Product 1

HCID 67202049HCID 67202049, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a refluxing suspension of amide E3 (7.89 g, 20.00 mmol) in 2:1 EtOH:H2O (500 mL) were sequentially added Fe dust (4.40 g, 79 mmol) and c.HCl (2% v/v, 10 mL), and the resulting mixture refluxed for ˜14 h. After this time, the hot reaction mixture was filtered through a pad of Celite, and the solvent was removed under reduced pressure. The residue was re-dissolved in hot H2O, and the resulting suspension filtered through a pad of Celite. Solvent was removed under reduced pressure, and the residue dried via three MeOH azeotrope cycles. The resulting residue was reprecipitated from acidified MeOH:EtOAc to give amine E4 as an amorphous tan solid (0.95 g, 12%); 1H NMR (400 MHz, DMSO): δ 12.71 (br s, 1H, pyrimidinyl-N+—H), 10.55 (br s, 1H, ArC(O)NHAr), 9.95 (s, 1H, ArNHAr), 8.10-7.40 (m, 7H, ArH & ArNH2), 7.32 (m, 1H, ArH), 6.77 (d, J=8.30 Hz, 2H, ArH), 6.18 (s, 1H, ArH), 2.28 (s, 3H, ArCH3); LCMS (APCI+): 335 (100%).

Workup

  1. filtrationAfter this time, the hot reaction mixture was filtered through a pad of Celite
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was re-dissolved in hot H2O
  4. filtrationthe resulting suspension filtered through a pad of Celite
  5. customSolvent was removed under reduced pressure
  6. dry with materialthe residue dried via three MeOH azeotrope cycles
  7. customThe resulting residue was reprecipitated

Sources & evidence

ORD record
ord-4e4e50df871742bdabdd7cab0eeaad25
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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