2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine → 8-(5-Amino-6-methyl-pyridin-3-yl)-1-(3-chloro-1-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445646Notes

Reaction equation

HRID 445646 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.[CH3:24][C:25]1[C:30]([NH2:31])=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][N:26]=1>>[NH2:31][C:30]1[CH:29]=[C:28]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]5[C:16]([Cl:21])=[N:17][N:18]([CH3:20])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)[CH:27]=[N:26][C:25]=1[CH3:24]

Participants

3

Reactant 2

HCID 596196372-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amineHCID 596197258-bromo-1-(3-chloro-1-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Product 1

HCID 596198578-(5-Amino-6-methyl-pyridin-3-yl)-1-(3-chloro-1-methyl-1H-pyrazol-4-yl)-3-methyl-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 2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylamine (Stage 88.1.1) to give the title compound as a white solid. (HPLC: tR 2.14 min (Method A); M+H=420 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.99 (s, 1H), 8.38 (s, 1H), 8.13-8.10 (m, 1H), 7.80-7.77 (m, 1H), 7.75-7.73 (m, 1H), 7.48-7.47 (m, 1H), 7.08-7.06 (m, 1H), 5.21-5.16 (m, br, 2H), 3.99 (s, 3H), 3.59 (s, 3H), 2.30 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-23d98a8d5a2f4406aa57abcc79241bdb
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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