Water → tert-butyl (1-(4-(2-(2-aminopyridin-3-yl)-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamate

HRID 1852900Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[C:5]([N+:27]([O-])=O)=[CH:4][CH:3]=1.[NH2:30][C:31]1[N:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].O>CS(C)=O.CO>[NH2:30][C:31]1[C:32]([C:33]2[N:8]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17][CH2:16]4)=[CH:11][CH:10]=3)[C:6]3=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=[C:5]3[N:27]=2)=[CH:35][CH:36]=[CH:37][N:38]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of tert-butyl (1-{4-[(6-chloro-3-nitropyridin-2-yl)amino]phenyl}cyclobutyl)carbamate (10 g, 24 mmol) in DMSO/MeOH (4:1, 200 mL), were added 2-aminonicotinaldehyde (3.5 g, 29 mmol) and sodium dithionite (16 g, 93 mmol) and the mixture was heated for 48 h at 100° C. The mixture was poured into water and the solid was collected by filtration. The solid was purified by silica gel column chromatography (dichloromethane/ethyl acetate, 10:0 to 0:10) to give the titled compound as a white solid (2.5 g, 21%).

Workup

filtrationthe solid was collected by filtration
customThe solid was purified by silica gel column chromatography (dichloromethane/ethyl acetate, 10:0 to 0:10)

Sources & evidence

ORD record: ord-e9246d65e63d45288045b70075aa08d4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962619B2

Reaction notes

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