8-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one → HCID 59619696, compound

HRID 445744Notes

Reaction equation

HRID 445744 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.[CH2:24]([NH:26][C:27]1[C:32]([CH2:33][O:34][CH3:35])=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1)[CH3:25]>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:30]5[CH:29]=[N:28][C:27]([NH:26][CH2:24][CH3:25])=[C:32]([CH2:33][O:34][CH3:35])[CH:31]=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-oneHCID 59619744HCID 59619744, compound

Product 1

HCID 59619696HCID 59619696, 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 (stage 205.1.1, 0.067 mmol) and ethyl-[3-methoxymethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-amine (Stage 206.1.1) to give the title compound as a yellow solid. (HPLC: tR 2.20 min (Method A); M+H=458 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.90 (s, 1H), 8.22-8.18 (m, 1H), 8.13 (s, 1H), 8.05-8.00 (m, 1H), 7.88-7.84 (m, 1H), 7.45-7.40 (m, 2H), 6.09 (t, 1H), 4.38-4.30 (m, 2H), 3.92 (s, 3H), 3.56 (s, 3H), 3.45-3.37 (m, 2H), 3.33 (s, 3H), 1.95 (s, 3H), 1.14 (t, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-9918971a2e794a29b393b2997484876c
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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