4-((N,N-Dimethylamino)methyl)phenylboronic acid pinacol ester → 6-{4-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-{[6-methyl-4-(1-methylethyl)-2-oxo-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide

HRID 85425

反応式

HRID 85425 の反応式
Br[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:28])[NH:20][C:21]([CH3:27])=[CH:22][C:23]=2[CH:24]([CH3:26])[CH3:25])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[CH3:29][N:30]([CH3:47])[CH2:31][C:32]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][CH:33]=1>>[CH3:29][N:30]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:2]2[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]3[C:19](=[O:28])[NH:20][C:21]([CH3:27])=[CH:22][C:23]=3[CH:24]([CH3:25])[CH3:26])=[O:15])[C:5]3[CH:6]=[N:7][N:8]([CH:11]([CH3:12])[CH3:13])[C:9]=3[CH:10]=2)=[CH:34][CH:33]=1)[CH3:47]

参加物

3

反応物 2

HCID 34604594-((N,N-Dimethylamino)methyl)phenylboronic acid pinacol esterHCID 545966296-bromo-1-(1-methylethyl)-N-{[6-methyl-4-(1-methylethyl)-2-oxo-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide

生成物 1

HCID 545966246-{4-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-{[6-methyl-4-(1-methylethyl)-2-oxo-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide

実験手順

The title compound was prepared in a similar manner as described for example 8 from 6-bromo-1-(1-methylethyl)-N-{[6-methyl-4-(1-methylethyl)-2-oxo-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide (90 mg, 0.202 mmol) and dimethyl{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}amine (90 mg, 0.303 mmol). The product was collected as a white solid (54 mg, 49%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.48 (br. s., 1H) 8.69 (br. s., 1H) 8.37 (s, 1H) 8.10 (s, 1H) 7.86 (s, 1H) 7.82 (s, 1H) 7.80 (s, 1H) 7.42 (s, 1H) 7.40 (s, 1H) 6.02 (s, 1H) 5.17 (dt, J=13.14, 6.57 Hz, 1H) 4.47 (d, J=4.80 Hz, 2H) 3.44 (s, 2H) 3.24 (dt, J=13.71, 6.92 Hz, 1H) 2.17 (s, 6H) 2.15 (s, 3H) 1.51 (s, 3H) 1.49 (s, 3H) 1.11 (s, 3H) 1.09 (s, 3H). LC-MS (ES) m/z=500.1 [M+H]+

後処理

  1. customThe product was collected as a white solid (54 mg, 49%)

出典と根拠

ORDレコード
ord-d64d44839ef14436a4a407b2f758e687
出典データセット
uspto-grants-2014_09
特許番号
US08846935B2

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