Tetrahydrofuran → HCID 131724911, compound

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](C#N)[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1Cl.C([N:33]([CH2:36]C)CC)C.[O:38]1CCC[CH2:39]1>>[C:36]([CH:22]1[CH2:21][O:20][CH:19]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:39]([C:26]4[O:25][CH:29]=[CH:28][CH:27]=4)=[O:38])[CH:7]=[CH:6][CH:5]=3)=[N:9]2)[CH2:24][CH2:23]1)#[N:33]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 1378562-Chlorofuran

HCID 22480146HCID 22480146, compound

Product 1

HCID 131724911HCID 131724911, compound

Procedure

To a solution of 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.300 g, 0.94 mmol) in tetrahydrofuran (10 mL), was added 2-furyl chloride (0.139 mL, 1.41 mmol) and triethyl amine (0.655 mL, 4.7 mmol). After stirring at room temperature overnight, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was dried under vacuum and the title product was purified by column chromatography (SiO2, 20–30% ethyl acetate in hexanes) (0.370 g, 95%): ES-MS (m/z) 413 [M+H]+.