HCID 59619673, compound → HCID 59619843, compound

HRID 445779Notes

Reaction equation

HRID 445779 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](=[O:45])[C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30][C:29]=1[NH:43][CH3:44])[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:32]5[CH:31]=[N:30][C:29]([NH:43][CH3:44])=[C:28]([CH:33]=5)[C:27]([NH:26][CH2:24][CH3:25])=[O:45])[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 59619673HCID 59619673, compoundHCID 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 59619843HCID 59619843, 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 N-ethyl-2-methylamino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinamide (Stage 242.1.1) to give the title compound as a yellowish foam. (HPLC: tR 2.17 min (Method A); M+H=471 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.92 (s, 1H), 8.58 (t, 1H), 8.25-8.20 (m, 2H), 8.11-8.06 (m, 2H), 8.05-8.02 (m, 1H), 7.96-7.92 (m, 1H), 7.47-7.44 (m, 1H), 3.89 (s, 3H), 3.57 (s, 3H), 3.40-3.19 (m, 2H), 2.93 (d, 3H), 1.97 (s, 3H), 1.15 (t, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-8b767f292b634c0ea9c16d273b2426b0
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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