5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amine → 8-(6-Amino-5-trifluoromethyl-pyridin-3-yl)-1-(1,3-dimethyl-1h-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445571Notes

Reaction equation

HRID 445571 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.[NH2:24][C:25]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][N:26]=1>>[NH2:24][C:25]1[N:26]=[CH:27][C:28]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]5[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)=[CH:29][C:30]=1[C:31]([F:34])([F:32])[F:33]

Participants

3

Reactant 2

HCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 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 596199928-(6-Amino-5-trifluoromethyl-pyridin-3-yl)-1-(1,3-dimethyl-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-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A, 40 mg, 0.105 mmol) and 2-amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester (stage 25.1.1, 37 mg, 0.128 mmol) to give the title compound as a pinkish solid. (HPLC: tR 2.40 min (Method A); M+H=454 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.93 (s, 1H), 8.43-8.36 (m, 1H), 8.16-8.11 (m, 1H), 8.09-8.02 (m, 1H), 7.97-7.90 (m, 1H), 7.76-7.70 (m, 1H), 7.45-7.39 (m, 1H), 6.76 (s, br, 2H), 3.88 (s, 3H), 3.56 (s, 3H), 1.95 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-de61b85b4b954ab7844e797630b23edf
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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