Tetrahydrofuran → HCID 16116818, compound

HRID 2264197Notes

Reaction equation

HRID 2264197 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:10][C:11]([NH2:15])=[C:12]([NH2:14])[CH:13]=1.C1C[O:25][CH2:24]C1.C(N1C=CN=C1)(N1C=CN=C1)=O>>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[C:12]2[NH:14][C:24](=[O:25])[NH:15][C:11]2=[N:10][C:9]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 595959543''-Fluoro-3,2':3',4''-terpyridine-5',6'-diamine2×

Product 1

HCID 16116818HCID 16116818, compoundYield 17%

Procedure

To a solution of 3″-fluoro-3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 1, 158 mg, 0.56 mmol) in THF (5 mL) Et3N (156 μL, 1.12 mmol) and carbonyldiimidazole (182 mg, 1.12 mmol) were added sequentially. The reaction mixture was heated to reflux for 4 h and then the solvent was removed under reduced pressure. Flash chromatography of the resulting crude oil (CH2Cl2/EtOH/aq NH3 60:8:1 to 40:8:1) followed by reverse phase chromatography (0% CH3CN in H2O to 25% CH3CN in H2O) gave the title compound as a white solid (29 mg, 17%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c67899eca6894aaa8b8eb0786526bef3
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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