Cyclohexanemethanol → {5-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-1,3,4-oxadiazol-2-yl}methanol

HRID 38873

Reaction equation

Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:16]=[C:15]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][N:12]3S(C2C=CC=CC=2)(=O)=O)=[N:5][N:4]=1.C1(C[OH:42])CCCCC1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[NH:21]1[C:22]2[C:18](=[C:17]([C:15]3[CH:14]=[C:13]4[C:9]([CH:10]=[N:11][NH:12]4)=[C:8]([C:6]4[O:7][C:3]([CH2:2][OH:42])=[N:4][N:5]=4)[CH:16]=3)[CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole (25 mg, 0.051 mmol), cyclohexylmethanol (17.48 mg, 0.153 mmol) and potassium carbonate (21.16 mg, 0.153 mmol) were placed in N-methyl-2-pyrrolidone (1 ml) and the mixture heated under microwave irradiation at 100° C. for 20 mins. Additional cyclohexylmethanol (17.48 mg, 0.153 mmol) was added and the mixture heated at 110° C. for 20 mins, followed by 110° C. for a further 20 mins. The solvent was removed and the residue purified by Mass Directed Automated Preparative HPLC to give the title compound as a white solid (5 mg).

Workup

temperaturethe mixture heated at 110° C. for 20 mins
customThe solvent was removed
customthe residue purified by Mass Directed Automated Preparative HPLC

Sources & evidence

ORD record: ord-a8aed5489aee458d9214f40f1d9238cf
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524751B2

Linked notes

Loading…