N,N'-Dimethylethylenediamine → Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl]-1,4-diazepane-1-carboxylate

HRID 57889

Reaction equation

Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)[CH:5]=[N:4][CH:3]=1.[Cl:22][C:23]1[N:28]=[CH:27][C:26]2[CH:29]=[N:30][NH:31][C:25]=2[CH:24]=1.CNCCNC.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I>[Cl:22][C:23]1[N:28]=[CH:27][C:26]2[CH:29]=[N:30][N:31]([C:2]3[N:7]=[C:6]([N:8]4[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]4)[CH:5]=[N:4][CH:3]=3)[C:25]=2[CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of tert-butyl 4-(6-bromopyrazin-2-yl)-1,4-diazepane-1-carboxylate (0.45 g, 1.26 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (192 mg, 1.26 mmol) in dioxane (10 mL) was added CuI (19 mg, 0.1 mmol), N1,N2-dimethylethane-1,2-diamine (6.3 mmol, 0.55 g), K2CO3(3.78 mmol, 0.53 g). The reaction mixture was heated at 100° C., which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude material was purified by silica gel chromatography using petroleum ether/ethyl acetate (5% to 50%) as eluting solvents to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl)-1,4-diazepane-1-carboxylate as yellow solid (0.4 g, 74%). MS (ESI) m/z: δ 430 [M+H]+.

Workup

customAfter completion of the reaction, it
concentrationwas concentrated under reduced pressure
customThe crude material was purified by silica gel chromatography
washas eluting solvents

Sources & evidence

ORD record: ord-eccdae8215514db682f3351f33148b02
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Linked notes

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