2-(Pyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine → n-Ethyl-n-methyl-2-{3-methyl-4-[3-methyl-2-oxo-8-(2-pyrrolidin-1-yl-pyrimidin-5-yl)-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-pyrazol-1-yl}-acetamide

HRID 445693Notes

Reaction equation

HRID 445693 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:29])[C:13](=[O:28])[N:14]([C:15]4[C:16]([CH3:27])=[N:17][N:18]([CH2:20][C:21]([N:23]([CH2:25][CH3:26])[CH3:24])=[O:22])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[N:30]1([C:35]2[N:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][N:36]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH2:25]([N:23]([CH3:24])[C:21](=[O:22])[CH2:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:38]5[CH:39]=[N:40][C:35]([N:30]6[CH2:31][CH2:32][CH2:33][CH2:34]6)=[N:36][CH:37]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:29])[C:13]2=[O:28])[C:16]([CH3:27])=[N:17]1)[CH3:26]

Participants

3

Reactant 2

HCID 164142242-(Pyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidineHCID 596200282-[4-(8-Bromo-3-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-n-ethyl-n-methyl-acetamide2×

Product 1

HCID 59620021n-Ethyl-n-methyl-2-{3-methyl-4-[3-methyl-2-oxo-8-(2-pyrrolidin-1-yl-pyrimidin-5-yl)-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-pyrazol-1-yl}-acetamide

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 2-[4-(8-bromo-3-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-N-ethyl-N-methyl-acetamide (Intermediate P) and 2-(pyrrolidin-1-yl)pyrimidine-5-boronic acid pinacol ester (Frontier Scientific, Logan, USA, 37 mg, 0.132 mmol) to give the title compound as an off-white solid. (HPLC: tR 2.53 min (Method A); M+H=526 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) cis&trans amide 8.92 (s, 1H), 8.59-8.55 (m, 2H), 8.08-8.01 (m, 2H), 7.88-7.84 (m, 1H), 7.68-7.63 (m, 1H), 5.23-5.15 (m, 1H), 5.11-5.04 (m, 1H), 3.57 (s, 3H), 3.53-3.21 (m, 6H), 3.01, 2.83 (2×s, 3H), 1.97-1.89 (m, 4H), 1.94, 1.93 (2×s, 3H), 1.17, 0.99 (2×t, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-b517e67caf9e4a24820ad4e4dc52dc40
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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