N,N'-Dimethylethylenediamine → tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-4-hydroxyazepane-1-carboxylate

HRID 57950Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]2([OH:22])[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]=[CH:4][CH:3]=1.[Cl:23][C:24]1[N:29]=[CH:28][C:27]2[CH:30]=[N:31][NH:32][C:26]=2[CH:25]=1.C([O-])([O-])=O.[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[Cl:23][C:24]1[N:29]=[CH:28][C:27]2[CH:30]=[N:31][N:32]([C:2]3[N:7]=[C:6]([C:8]4([OH:22])[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]=[CH:4][CH:3]=3)[C:26]=2[CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-4-hydroxyazepane-1-carboxylate (792 mg, 2.4 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (300 mg, 1.94 mmol) in 1,4-dioxane (20 mL) was added CuI (150 mg, 0.78 mmol), K2CO3 (1.08 g, 7.8 mmol), and N1,N2-dimethylethane-1,2-diamine (138 mg, 1.56 mmol). The mixture was heated at 100° C. for 3 hours, which was monitored by LCMS. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude was purified by silica gel chromatography using petroleum ether/EtOAc (4/1) to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-4-hydroxyazepane-1-carboxylate as a white solid (550 mg, 58%). MS (ESI) m/z: 444 [M+H]+.

Workup

customAfter completion of the reaction
concentrationthe reaction mixture was concentrated under reduced pressure
customThe crude was purified by silica gel chromatography

Sources & evidence

ORD record: ord-f75735d467f34fe0acb18f50643cf818
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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