4-(tert-Butoxycarbonylaminomethyl)phenylboronic acid → Tert-butyl 4-(6-((2-(cyclopentyloxy)ethyl)amino)imidazo[1,2-b]pyridazin-3-yl)benzylcarbamate

HRID 870719Notes

Reaction equation

HRID 870719 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[CH:15]1([O:14][CH2:13][CH2:12][NH:11][C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([C:32]4[CH:33]=[CH:34][C:29]([CH2:28][NH:27][C:25](=[O:26])[O:24][C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:30][CH:31]=4)=[CH:3][N:4]=3)[N:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 38631634-(tert-Butoxycarbonylaminomethyl)phenylboronic acidHCID 866964223-bromo-N-(2-(cyclopentyloxy)ethyl)imidazo[1,2-b]pyridazin-6-amine

Product 1

HCID 86696423Tert-butyl 4-(6-((2-(cyclopentyloxy)ethyl)amino)imidazo[1,2-b]pyridazin-3-yl)benzylcarbamateYield 70%

Procedure

The 3-bromo-N-(2-(cyclopentyloxy)ethyl)imidazo[1,2-b]pyridazin-6-amine was coupled with (4-(((tert-butoxycarbonyl)amino)methyl)phenyl)boronic acid under the Suzuki coupling conditions as described in example 5.6.76, Part B to obtain 70% product.

Sources & evidence

ORD record
ord-e48d372006584011a22754f4518a330c
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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