4-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine → HCID 59619665, compound

HRID 445746Notes

Reaction equation

HRID 445746 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][N:25]1[CH2:30][CH2:29][O:28][C:27]2[CH:31]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:33]=[N:34][C:26]1=2>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:32]5[CH:33]=[N:34][C:26]6[N:25]([CH3:24])[CH2:30][CH2:29][O:28][C:27]=6[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 242296534-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazineHCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Product 1

HCID 59619665HCID 59619665, 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 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (ABCR, Karlsruhe, Germany) to give the title compound as a yellow foam. (HPLC: tR 2.15 min (Method A); M+H=442 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.90 (s, 1H), 8.13 (s, 1H), 8.03-7.99 (m, 1H), 7.89-7.82 (m, 2H), 7.40-7.37 (m, 1H), 6.97-6.94 (m, 1H), 4.25 (t, 2H), 3.92 (s, 3H), 3.56 (s, 3H), 3.47 (t, 2H), 3.06 (s, 3H), 1.95 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-88dbc881bfdb4bd68b2347e08ded18d4
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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