tert-butyl Methyl(3-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbaMate → 1-(3-Chloro-1-methyl-1h-pyrazol-4-yl)-3-methyl-8-(5-methyl-6-methylamino-pyridin-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445680Notes

Reaction equation

HRID 445680 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([Cl:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[C:24]([N:31](C)[C:32]1[N:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:33]=1[CH3:47])(OC(C)(C)C)=O>>[Cl:21][C:16]1[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:35]5[CH:36]=[N:37][C:32]([NH:31][CH3:24])=[C:33]([CH3:47])[CH:34]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])=[CH:19][N:18]([CH3:20])[N:17]=1

Participants

3

Reactant 2

HCID 44755181tert-butyl Methyl(3-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbaMateHCID 596197258-bromo-1-(3-chloro-1-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Product 1

HCID 596199781-(3-Chloro-1-methyl-1h-pyrazol-4-yl)-3-methyl-8-(5-methyl-6-methylamino-pyridin-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-1-(3-chloro-1-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate K) and 6-(N-boc-methylamino)-5-methylpyridine-3-boronic acid pinacol ester (Combi-Blocks, San Diego, USA, 58.8 mg, 0.176 mmol) to give crude boc-protected title compound that was treated for 30 min at rt with trifluoroacetic acid (0.5 ml) and then purified by prep. HPLC to give the title compound as an off-white foam. (HPLC: tR 2.24 min (Method A); M+H=434 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.92 (s, 1H), 8.40 (s, 1H), 8.14-8.12 (m, 1H), 8.05-8.03 (m, 1H), 7.90-7.85 (m, 1H), 7.38-7.37 (m, 2H), 6.28-6.20 (br, 1H), 4.01 (s, 3H), 3.58 (s, 3H), 2.88 (m, 3H), 2.11 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-6f9b44ab964c46549d8257feb9a5db8e
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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