Acetonitrile → HCID 86583568, compound

HRID 1016794Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[C:20]([CH:22]=[CH2:23])[CH:19]=[C:18]([O:24][CH2:25][CH3:26])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].[B-](F)(F)(F)F.[N:32]#[O+:33].[C:34](#[N:36])[CH3:35]>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[C:20]([C:22]3[N:32]([OH:33])[C:34]([CH3:35])=[N:36][CH:23]=3)[CH:19]=[C:18]([O:24][CH2:25][CH3:26])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

Reactant 3

HCID 6342Acetonitrile2×

HCID 11137142Nitrilooxonium tetrafluoroborate

HCID 131722621HCID 131722621, compound

Product 1

HCID 86583568HCID 86583568, compoundYield 38%

Conditions

Temperature: 0 °C

Procedure

A solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-vinyl-phenyl)-acetate (300 mg, 0.856 mmol) obtained in Example 236.2 in acetonitrile (2 ml) was slowly added dropwise at −30° C. to a solution of nitrosyl tetrafluoroborate (112 mg, 0.942 mmol) in acetonitrile (3 ml). The mixture was stirred for 2 h. at 0° C. and for 1.5 h. at room temperature. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, CH2Cl2→CH2Cl2/MeOH 4:1). There were obtained 135 mg (38%) of ethyl (RS)-(4-cyano-phenylamino)-[3-ethoxy-5-(3-hydroxy-2-methyl-3H-imidazol-4-yl)-phenyl]-acetate as a yellowish foam; MS: 421 ([M+H]+).

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by chromatography (SiO2, CH2Cl2→CH2Cl2/MeOH 4:1)

Sources & evidence

ORD record: ord-cb534a4924184e7593d92a2ffb754e76
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476264B2

Reaction notes

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