Diisopropylcarbodiimide → HCID 178505990, compound

HRID 2264226Notes

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.[N:22]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=[C:23]=S.C(N=C=NC(C)C)(C)C>C(O)C>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[C:12]2[N:14]=[C:23]([NH:22][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[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

Conditions

Temperature: 50 °C

Procedure

To a solution of 3″-fluoro-3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 1, 0.1 g, 0.356 mmol) and 3-isothiocyanatopyridine (0.06 mL, 0.534 mmol) in ethanol (2 mL), 1,3-diisopropylcarbodiimide (0.083 mL, 0.534 mmol) was added. The mixture was heated at 50° C. for 2 h. After cooling at room temperature, the solvent was evaporated. The crude mixture was purified by silica gel flash chromatography (95:5 dichloromethane/methanol) to give the title compound (0.045 g, 33% of yield).

Workup

temperatureAfter cooling at room temperature
customthe solvent was evaporated
customThe crude mixture was purified by silica gel flash chromatography (95:5 dichloromethane/methanol)

Sources & evidence

ORD record: ord-b598f26eb10c4ae0ba7aaa53c7db8dea
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855202B2

Reaction notes

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