8-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one → N-{2-Chloro-5-[1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl]-pyridin-3-yl}-acetamide

HRID 445757Notes

Reaction equation

HRID 445757 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]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[Cl:24][C:25]1[C:30]([NH:31][C:32](=[O:34])[CH3:33])=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][N:26]=1>>[Cl:24][C:25]1[C:30]([NH:31][C:32](=[O:34])[CH3:33])=[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]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)=[CH:27][N:26]=1

Participants

3

Reactant 2

HCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×HCID 59619969N-[2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-acetamide

Product 1

HCID 59619736N-{2-Chloro-5-[1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl]-pyridin-3-yl}-acetamide

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-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A) and N-[2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-acetamide (Stage 222.1.1) to give the title compound as an off-white solid. (HPLC: tR 2.33 min (Method A); M+H=462 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.80 (s, 1H), 9.01 (s, 1H), 8.34-8.28 (m, 2H), 8.17-8.11 (m, 2H), 7.95-7.90 (m, 1H), 7.61-7.58 (m, 1H), 3.92 (s, 3H), 3.59 (s, 3H), 2.18 (s, 3H), 1.93 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-c2b5468415424dfeadd6f2600b393e2a
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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