Hydrochloric Acid → HCID 178465565, compound

HRID 386669Notes

Reaction equation

HRID 386669 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH:30]=[CH:29][C:28]([NH:31][C:32](=[NH:34])[CH3:33])=[CH:27][C:15]=4[C:16](=[O:26])[C:17]=3[O:18]CC3C=CC=CC=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[ClH:35]>CO.[Pd]>[ClH:35].[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH:30]=[CH:29][C:28]([NH:31][C:32](=[NH:34])[CH3:33])=[CH:27][C:15]=4[C:16](=[O:26])[C:17]=3[OH:18])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178465564HCID 178465564, compound

Product 1

HCID 178465565HCID 178465565, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

2-[(4-(imidazol-1-yl)-phenyl]-3-benzyloxy-6-[(1-iminoethyl)amino]-4H-1-benzopyran-4-one (1.6 g; 3.34 mmol) was suspended in methanol (100 mL), 3 mL of MeOH saturated with HCl were added to the reaction mixture then 10% Pd/C (160 mg.) was added. The reaction mixture was left under hydrogen bubbling for 4 hours, then the catalyst was filtered off. The solvent was removed and the remaining solid suspended in diethyl ether, then filtered. The titled compound was obtained as a yellow solid, yield: 75%; m.p.: 311.7-312.1° C.; Elem. anal.: C20H16N4O3.HCl, Theory: C, 55.44; H, 4.19; N, 12.93. Found: C, 56.09; H, 4.34; N, 13.22. TLC (8/2 Chloroform/Methanol) Rf: 0.11; IR (KBr): 2996, 2871, 1568, 1592 cm−1; 1H-NMR (d6-DMSO): 11.89 (s, 1H); 10.27 (s, 1H); 9.81 (s, 1H) 9.71 (s, 1H); 8.81 (s, 1H); 8.50 (d, 2H); 8.4 (d, 1H); 8.01 (m, 4H); 7.93 (d, 1H); 7.77 (dd, 1H); 2.58 (d, 2H); 1.28 (m, 1H); MS (EI) 401 (M+1).

Workup

  1. filtrationthe catalyst was filtered off
  2. customThe solvent was removed
  3. filtrationfiltered

Sources & evidence

ORD record
ord-5aed1cf73d2045a7bf327cb39cedf20d
Source dataset
uspto-grants-2013_02
Patent number
US08372866B2

Reaction notes

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