Sodium Bicarbonate → Tert-butyl 4-[(3-chloro-5-cyanopyridin-2-yl)amino]butanoate

HRID 1631015Notes

Reaction equation

Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)(O)[O-].[Na+].[Cl:18][C:19]1[C:20](Cl)=[N:21][CH:22]=[C:23]([CH:26]=1)[C:24]#[N:25]>O1CCOCC1>[Cl:18][C:19]1[C:20]([NH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[N:21][CH:22]=[C:23]([C:24]#[N:25])[CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of tert-butyl 4-aminobutanoate hydrochloride (Bachem F-3755, 8.54 g, 28.9 mmol), sodium bicarbonate (6.0 g, 72.2 mmol) and 5,6-dichloronicotinonitrile (Bionet GC-0755, 5.0 g, 28.9 mmol) was prepared in dioxane under nitrogen, and then heated at 50° C. for 16 hours. The reaction mixture was filtered to remove inorganic solids and filtrate was concentrated under reduced pressure. After purification by flash chromatography (silica, pet ether/EtOAc), the title compound was obtained as a white powder. 1H NMR (DMSO-d6, 400 MHz) δ 8.40 (1H, d), 8.05 (1H, d), 7.58 (1H, t), 3.42 (2H, m), 2.21 (2H, t), 1.76 (2H, m), 1.37 (9H, s).

Workup

filtrationThe reaction mixture was filtered
customto remove inorganic solids and filtrate
concentrationwas concentrated under reduced pressure
customAfter purification by flash chromatography (silica, pet ether/EtOAc)

Sources & evidence

ORD record: ord-f35fb2d6fab04ef8a816962df0ead284
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791142B2

Reaction notes

Loading…