8-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one → HCID 49835567, compound

HRID 445609Notes

Reaction equation

HRID 445609 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.[CH:24]1([O:28][C:29]2[CH:30]=[N:31][CH:32]=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:34]=2)[CH2:27][CH2:26][CH2:25]1>>[CH:27]1([CH2:24][O:28][C:29]2[CH:34]=[C:33]([C:2]3[CH:11]=[CH:10][C:9]4[N:8]=[CH:7][C:6]5[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]6[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=6)[C:5]=5[C:4]=4[CH:3]=3)[CH:32]=[N:31][CH:30]=2)[CH2:26][CH2:25]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 596197653-(Cyclobutyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 49835567HCID 49835567, compound

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 3-cyclobutoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (Stage 60.1.1) to give the title compound as a white solid. (HPLC: tR 2.39 min (Method A); M+H=441 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.99-8.98 (m, 1H), 8.32-8.27 (m, 2H), 8.15 (s, 1H), 8.13-8.09 (m, 1H), 8.02-7.97 (m, 1H), 7.59-7.57 (m, 1H), 7.37-7.35 (m, 1H), 4.02-3.92 (m, 2H), 3.90 (s, 3H), 3.58 (s, 3H), 1.96 (s, 3H), 1.32-1.23 (m, 1H), 0.65-0.59 (m, 2H), 0.41-0.36 (m, 2H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-e2417510a56e4383badb11da72f79033
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…