HCID 59619706, compound → HCID 59619905, compound

HRID 445785Notes

Reaction equation

HRID 445785 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][O:27][CH2:28][C:29]1[C:30]([NH:44][CH3:45])=[N:31][CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1>>[CH:20]([N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:33]5[CH:32]=[N:31][C:30]([NH:44][CH3:45])=[C:29]([CH2:28][O:27][CH3:26])[CH:34]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:25])[C:13]2=[O:24])[C:16]([CH3:23])=[N:17]1)([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 59619706HCID 59619706, compoundHCID 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 59619905HCID 59619905, compound

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) and [3-methoxymethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-methyl-amine (Stage 248.1.1) to give the title compound as a yellowish foam. (HPLC: tR 2.24 min (Method A); M+H=472 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.90 (s, 1H), 8.20 (s, 1H), 8.15-8.13 (m, 1H), 8.05-8.02 (m, 1H), 7.85-7.81 (m, 1H), 7.48-7.45 (m, 1H), 7.43-7.41 (m, 1H), 6.13 (q, 1H), 4.55 (hp, 1H), 4.30 (s, 2H), 3.57 (s, 3H), 3.31 (s, 3H), 2.86 (d, 3H), 1.96 (s, 3H), 1.49-1.45 (m, 6H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-32ebb5d6a8094ffb8ed8a1bebc0e8b6f
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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