Tetrafluoro-m-phenylenediamine dihydrochloride → 2,5-Bis[3-methoxy-4-(2-pyridylimino)aminophenyl]furan

HRID 49540Notes

Reaction equation

HRID 49540 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([O:20][CH3:21])[CH:14]=3)=[CH:11][CH:12]=2)=[CH:4][C:3]=1[O:22][CH3:23].[C:24]1([NH2:35])[C:29](F)=[C:28](F)[C:27](F)=[C:26]([NH2:33])C=1F.Cl.Cl>CN(C=O)C.O>[CH3:23][O:22][C:3]1[CH:4]=[C:5]([C:8]2[O:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([N:19]=[N:33][C:26]4[CH:27]=[CH:28][CH:29]=[CH:24][N:35]=4)=[C:15]([O:20][CH3:21])[CH:14]=3)=[CH:11][CH:12]=2)[CH:6]=[CH:7][C:2]=1[N:1]=[N:33][C:26]1[CH:27]=[CH:28][CH:29]=[CH:24][N:35]=1

Participants

4

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 206373562,5-Bis(4-amino-3-methoxyphenyl)furan

Product 1

HCID 206373412,5-Bis[3-methoxy-4-(2-pyridylimino)aminophenyl]furanYield 70%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

2,5-Bis[3-methoxy-4-(2-pyridylimino)aminophenyl]furan (4o, DB746) was prepared according to the procedure for 4f using diamine 3i and S-(2-naphthylmethyl)-2-pyridylthioimidate hydrobromide as starting materials. Free base: yellow crystalline solid, mp 212-213° C. (DMF/H2O). Yield: 70%. 1H NMR (DMSO-d6): 3.82 (s, 6H), 6.89 (d, 2H), 6.98 (s, 2H), 7.38 (m, 4H), 7.54 (dd, 2H), 7.95 (dd, 2H), 8.32 (d, 2H), 8.62 (d, 2H). Dihydrochloride: yellow solid. 1H NMR (DMSO-d6): 3.97 (s, 6H), 7.36 (s, 2H), 7.47 (d, 2H), 7.62 (d, 4H), 7.85 (dd, 2H), 8.20 (d, 2H), 8.45 (d, 2H), 8.89 (d, 2H), 9.37 (br s, 2H), 10.10 (br s, 2H), 11.86 (br s, 2H). Anal. Calcd. for C30H26N6O.2.0HCl.1.0H2O (609.5): C, H, N, Cl.

Sources & evidence

ORD record
ord-567aa75c534e4d85afcdf3df29ba4fc5
Source dataset
uspto-grants-2004_03
Patent number
US06706754B2

Reaction notes

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