2-((5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)aMino)ethanol → 8-[6-(2-Hydroxy-ethylamino)-pyridin-3-yl]-3-methyl-1-(2-methyl-2H-pyrazol-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445566Notes

Reaction equation

HRID 445566 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:22])[C:13](=[O:21])[N:14]([C:15]4[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[CH:33][C:34]([NH:37][CH2:38][CH2:39][OH:40])=[N:35][CH:36]=2)O1>>[OH:40][CH2:39][CH2:38][NH:37][C:34]1[N:35]=[CH:36][C:31]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:22])[C:13](=[O:21])[N:14]([C:15]5[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 596198562-((5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)aMino)ethanolHCID 59620095HCID 59620095, compound2×

Product 1

HCID 596200738-[6-(2-Hydroxy-ethylamino)-pyridin-3-yl]-3-methyl-1-(2-methyl-2H-pyrazol-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-3-methyl-1-(2-methyl-2H-pyrazol-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate E, 65 mg, 0.181 mmol) and 2-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamino]-ethanol (stage 21.1.1, 82 mg, 0.218 mmol) to give the title compound as an off-white foam. (HPLC: tR 2.08 min (Method A); M+H=416 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.96 (s, 1H), 8.12-8.02 (m, 2H), 7.80-7.75 (m, 2H), 7.51-7.44 (m, 1H), 6.95-6.89 (m, 1H), 6.85-6.73 (br, 1H), 6.69 (s, 1H), 6.60-6.53 (m, 1H), 3.66 (s, 3H), 3.58 (s, 3H), 3.54-3.49 (m, 2H), 3.37-3.31 (m, 2H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-43ab1d17c40442a182fc12306e5fb32c
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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