5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine → 8-(5-Amino-pyridin-3-yl)-1-(1,3-dimethyl-1h-pyrazol-4-yl)-3-ethyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445780Notes

Reaction equation

HRID 445780 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH2:23][CH3:24])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[NH2:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=1>>[NH2:25][C:26]1[CH:31]=[C:30]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH2:23][CH3:24])[C:13](=[O:22])[N:14]([C:15]5[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)[CH:29]=[N:28][CH:27]=1

Participants

3

Reactant 2

HCID 438110685-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamineHCID 596200728-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-ethyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Product 1

HCID 596199098-(5-Amino-pyridin-3-yl)-1-(1,3-dimethyl-1h-pyrazol-4-yl)-3-ethyl-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-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-ethyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (stage 245.1.1) and 3-aminopyridine-5-boronic acid pinacol ester (Apollo Scientific, Cheshire, United Kingdom) to give the title compound as a white solid. (HPLC: tR 2.02 min (Method A); M+H=400 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.02 (s, 1H), 8.15 (s, 1H), 8.12-8.07 (m, 1H), 7.94-7.91 (m, 1H), 7.81-7.76 (m, 2H), 7.54-7.51 (m, 1H), 7.03-7.00 (m, 1H), 5.44 (s, 2H), 4.11 (q, 2H), 3.91 (s, 3H), 1.94 (s, 3H), 1.35 (t, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-6c817c7f310c4dc599b920ee6de12bfc
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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