Triethylamine → 5-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 510097Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[CH:13][CH:12]=3)[N:9]=[C:8]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:5]2=[N:6][CH:7]=1.C1N=CN([C:32](N2C=NC=C2)=[O:33])C=1.C(N(CC)CC)C>CN(C)C=O.O.C(=O)([O-])O.[Na+]>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]4[NH:17][C:32](=[O:33])[NH:18][C:14]4=[CH:13][CH:12]=3)[N:9]=[C:8]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

70 mg (0.20 mmol) of the compound from example 40A were initially charged in dimethylformamide (5 ml), then 161 mg (0.993 mmol) of N,N-carbonyldiimidazole and 0.33 ml (2.38 mmol) of triethylamine were added and the mixture was stirred at 100° C. overnight. The reaction mixture was subsequently diluted with water and saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The collected organic phases were dried over sodium sulfate, filtered and concentrated by rotary evaporation. Preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient) of the residue gave 38 mg (48% of theory) of the desired title compound in solid form.

Workup

extractionextracted twice with ethyl acetate
dry with materialThe collected organic phases were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record: ord-9157c7d7d10944888c23da0fb23c9002
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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