8-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one → HCID 59619742, compound

HRID 445623Notes

Reaction equation

HRID 445623 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.[CH3:24][O:25][CH2:26][CH2:27][N:28]1[C:36]2[C:31](=[N:32][CH:33]=[C:34](B3OC(C)(C)C(C)(C)O3)[CH:35]=2)[N:30]([CH3:46])[C:29]1=[O:47]>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:34]5[CH:35]=[C:36]6[N:28]([CH2:27][CH2:26][O:25][CH3:24])[C:29](=[O:47])[N:30]([CH3:46])[C:31]6=[N:32][CH:33]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])[C:16]([CH3:21])=[N:17]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 59619990HCID 59619990, compound

Product 1

HCID 59619742HCID 59619742, 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 1-(2-methoxy-ethyl)-3-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (Stage 69.1.1) to give the title compound as a white solid. (HPLC: tR 2.46 min (Method A); M+H=499 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.15-8.05 (m, 3H), 7.97-7.91 (m, 1H), 7.64-7.60 (m, 1H), 7.57-7.53 (m, 1H), 4.11-4.03 (m, 2H), 3.90 (s, 31-1), 3.67-3.62 (m, 2H), 3.57 (s, 3H), 3.36 (s, 3H), 3.23 (s, 3H), 1.98 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-832d33d731684a03a9c3bd788fcd940c
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…