tert-Butyl {[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]methyl}carbamate → HCID 59620031, compound

HRID 445768Notes

Reaction equation

HRID 445768 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.C([NH:31][CH2:32][C:33]1[CH:34]=[N:35][CH:36]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:38]=1)(OC(C)(C)C)=O>>[NH2:31][CH2:32][C:33]1[CH:38]=[C:37]([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:36]=[N:35][CH:34]=1

Participants

3

Reactant 2

HCID 46739732tert-Butyl {[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]methyl}carbamateHCID 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 59620031HCID 59620031, 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 3-(N-boc-aminomethyl)pyridine-5-boronic acid pinacol ester (Frontier Scientific, Logan, USA) to give the title compound as an off-white solid. (HPLC: tR 1.87 min (Method A); M+H=400 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.99 (s, 1H), 8.56-8.51 (m, 2H), 8.17-8.11 (m, 2H), 7.99-7.95 (m, 1H), 7.86-7.83 (m, 1H), 7.61-7.58 (m, 1H), 3.92 (s, 3H), 3.79 (s, 2H), 3.58 (s, 3H), 2.06-1.97 (br, 2H), 1.95 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-991e92cde42f430498d83ccdf28e5a33
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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