1-(Pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → N-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(isopropylamino)-2-(4-(3-pyridin-3-ylureido)phenyl)pyrimidin-5-yl)-3-(dimethylamino)propanamide

HRID 75445Notes

Reaction equation

HRID 75445 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[C:14]([NH:15][C:16](=[O:22])[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[C:13]([NH:23][CH:24]([CH3:26])[CH3:25])[N:12]=[C:11](Cl)[N:10]=1)[CH2:2]2.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35]([NH:37][C:38]2[CH:43]=[CH:42][C:41](B3OC(C)(C)C(C)(C)O3)=[CH:40][CH:39]=2)=[O:36])[CH:29]=1>>[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[C:14]([NH:15][C:16](=[O:22])[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[C:13]([NH:23][CH:24]([CH3:26])[CH3:25])[N:12]=[C:11]([C:41]3[CH:40]=[CH:39][C:38]([NH:37][C:35]([NH:34][C:30]4[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=4)=[O:36])=[CH:43][CH:42]=3)[N:10]=1)[CH2:2]2

Participants

3

Reactant 2

HCID 446075271-(Pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 86665900N-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-6-(isopropylamino)pyrimidin-5-yl)-3-(dimethylamino)propanamide

Product 1

HCID 68761191N-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(isopropylamino)-2-(4-(3-pyridin-3-ylureido)phenyl)pyrimidin-5-yl)-3-(dimethylamino)propanamide

Procedure

N-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(isopropylamino)-2-(4-(3-pyridin-3-ylureido)phenyl)pyrimidin-5-yl)-3-(dimethylamino)propanamide was prepared by Suzuki coupling using the general method from scheme 2 for the preparation of 6 using N-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-6-(isopropylamino)pyrimidin-5-yl)-3-(dimethylamino)propanamide (49, 0.050 g, 0.126 mmoles) and 1-(pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (52, 0.047 g, 0.139 mmoles). The crude product was purified by HPLC to provide the title compound as a yellow solid. Yield: 0.049 g (68%). HRMS; [M+H]+ Calc'd=574.3249, [M+H]+ Obs'd=574.3241.

Workup

  1. customN-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(isopropylamino)-2-(4-(3-pyridin-3-ylureido)phenyl)pyrimidin-5-yl)-3-(dimethylamino)propanamide was prepared by Suzuki coupling
  2. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-db780894d9d34c2bb3bde2a8564fda8e
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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