8-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one → HCID 59620015, compound

HRID 445777Notes

Reaction equation

HRID 445777 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:26]([CH2:40][O:41]C(=O)C)=[N:27][CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=1>>[Cl:24][C:25]1[CH:30]=[C:29]([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:28]=[N:27][C:26]=1[CH2:40][OH:41]

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 59619924HCID 59619924, compound

Product 1

HCID 59620015HCID 59620015, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 169.1 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 acetic acid 3-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylmethyl ester (Stage 238.1.1) to give the title compound as an off-white solid. (HPLC: tR 2.27 min (Method A); M+H=435 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.00 (s, 1H), 8.65-8.62 (m, 1H), 8.18-8.11 (m, 2H), 8.05-8.00 (m, 1H), 7.97-7.94 (m, 1H), 7.58-7.55 (m, 1H), 5.30 (t, 1H), 4.67 (d, 2H), 3.94 (s, 3H), 3.58 (s, 3H), 1.95 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-ec000412d01a441cab6c94dff63b2f66
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…