[6-(4-Methylpiperazin-1-yl)pyridin-3-yl]boronic acid → HCID 67816248, compound

HRID 1616805Notes

Reaction equation

HRID 1616805 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH:13][CH2:14][C:15]3[C:16](=[O:25])[NH:17][C:18]([CH3:24])=[CH:19][C:20]=3[CH2:21][CH2:22][CH3:23])=[O:12])[CH:10]=1)[N:7]([CH3:26])[CH:6]=[C:5]2[CH:27]([CH3:29])[CH3:28].[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]2[N:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=2)[CH2:33][CH2:32]1>>[CH3:26][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:40]3[CH:41]=[N:42][C:37]([N:34]4[CH2:33][CH2:32][N:31]([CH3:30])[CH2:36][CH2:35]4)=[CH:38][CH:39]=3)=[CH:10][C:9]=2[C:11]([NH:13][CH2:14][C:15]2[C:16](=[O:25])[NH:17][C:18]([CH3:24])=[CH:19][C:20]=2[CH2:21][CH2:22][CH3:23])=[O:12])[C:5]([CH:27]([CH3:29])[CH3:28])=[CH:6]1

Participants

3

Reactant 2

HCID 53398055[6-(4-Methylpiperazin-1-yl)pyridin-3-yl]boronic acidHCID 67816516HCID 67816516, compound

Product 1

HCID 67816248HCID 67816248, compoundYield 59.2%

Procedure

The title compound was prepared in the same manner as described for Example 2 using 5-bromo-1-methyl-3-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indole-7-carboxamide (480 mg, 1.05 mmol) and [6-(4-methyl-1-piperazinyl)-3-pyridinyl]boronic acid (320 mg, 1.45 mmol). Obtained 345 mg of the title compound (59% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (s, 1H), 8.41-8.48 (m, J=2.53 Hz, 2H), 7.86 (dd, J=2.53, 8.84 Hz, 1H), 7.76 (d, J=1.77 Hz, 1H), 7.26 (d, J=1.52 Hz, 1H), 7.08 (s, 1H), 6.92 (d, J=8.84 Hz, 1H), 5.90 (s, 1H), 4.37 (d, J=4.80 Hz, 2H), 3.68 (s, 3H), 3.48-3.56 (m, 4H), 3.20 (quin, J=6.76 Hz, 1H), 2.52-2.58 (m, 2H), 2.44 (br. s., 4H), 2.25 (s, 3H), 2.13 (s, 3H), 1.57 (qt, J=7.36, 7.56 Hz, 2H), 1.30 (d, J=6.82 Hz, 6H), 0.93 (t, J=7.33 Hz, 3H). MS (ES) [M+H]+ 555.1.

Workup

  1. customThe title compound was prepared in the same manner

Sources & evidence

ORD record
ord-c07878493fcd46e6b9ef2853ad02b3a1
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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