N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine → 8-(2-Dimethylamino-pyrimidin-5-yl)-1-(1-isopropyl-3-methyl-1h-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445550Notes

Reaction equation

HRID 445550 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:25])[C:13](=[O:24])[N:14]([C:15]4[C:16]([CH3:23])=[N:17][N:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH3:26][N:27]([CH3:43])[C:28]1[N:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1>>[CH3:26][N:27]([CH3:43])[C:28]1[N:33]=[CH:32][C:31]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:25])[C:13](=[O:24])[N:14]([C:15]5[C:16]([CH3:23])=[N:17][N:18]([CH:20]([CH3:21])[CH3:22])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)=[CH:30][N:29]=1

Participants

3

Reactant 2

HCID 16414215N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amineHCID 596200788-bromo-1-(1-isopropyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Product 1

HCID 596196988-(2-Dimethylamino-pyrimidin-5-yl)-1-(1-isopropyl-3-methyl-1h-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1-isopropyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate G, 50 mg, 0.125 mmol) and 2-dimethylamino-pyrimidine-5-boronic acid pinacol ester (Frontier Scientific, Logan, USA, 38 mg, 0.153 mmol) to give the title compound as a white solid. (HPLC: tR 2.68 min (Method A); M+H=443 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.93 (s, 1H), 8.46 (s, 2H), 8.20 (s, 1H), 8.09-8.02 (m, 1H), 7.91-7.84 (m, 1H), 7.38 (s, 1H), 4.60-4.51 (m, 1H), 3.56 (s, 3H), 3.13 (s, 6H), 1.97 (s, 3H), 1.49-1.44 (m, 6H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-377131e53b3c46c28ae029e7f0132859
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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