Triethylamine → HCID 86704979, compound

HRID 572168Notes

Reaction equation

Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[CH3:11][O:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[N:14]=1.C(N(CC)CC)C>CO>[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[O:28][C:25]1[CH:24]=[CH:23][C:22]([N:15]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:21]3[C:13]([O:12][CH3:11])=[N:14]2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 2-chloro-1H-benzimidazole (0.23 g), 4-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)phenol (0.24 g) and triethylamine (1.0 ml) was stirred under a nitrogen atmosphere at 160° C. for 7 hr. The reaction mixture was cooled to room temperature, and methanol was added to the reaction mixture. The precipitated solid was filtered off, silica gel was added to the filtrate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate). Then, it was purified by HPLC(C18) (mobile phase: water/acetonitrile (0.1% TFA-containing eluents)) to give the title compound (0.047 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe precipitated solid was filtered off
additionsilica gel was added to the filtrate
customthe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
customThen, it was purified by HPLC(C18) (mobile phase: water/acetonitrile (0.1% TFA-containing eluents))

Sources & evidence

ORD record: ord-0d5af448fed1429c8d6d5f8fbcf0788b
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029388B2

Reaction notes

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