1-Ethyl-1H-pyrazole-4-boronic acid, pinacol ester → (R)-6-(1-ethyl-1H-pyrazol-4-yl)-1-(6-(3-ethylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57839

反応式

HRID 57839 の反応式
[CH2:1]([N:3]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[N:4]1)[CH3:2].[CH2:17]([C@@H:19]1[CH2:24][NH:23][CH2:22][CH2:21][N:20]1C(OC(C)(C)C)=O)[CH3:18]>>[CH2:1]([N:3]1[CH:7]=[C:6]([C:22]2[N:23]=[CH:24][C:6]3[CH:5]=[N:4][N:3]([C:1]4[CH:2]=[CH:18][CH:17]=[C:19]([N:23]5[CH2:22][CH2:21][NH:20][C@H:19]([CH2:17][CH3:18])[CH2:24]5)[N:20]=4)[C:7]=3[CH:21]=2)[CH:5]=[N:4]1)[CH3:2]

参加物

3

反応物 2

HCID 113790451-Ethyl-1H-pyrazole-4-boronic acid, pinacol esterHCID 24728614(R)-1-Boc-2-ethylPiperazine

生成物 1

HCID 72715377(R)-6-(1-ethyl-1H-pyrazol-4-yl)-1-(6-(3-ethylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine収率 10%

実験手順

Following the procedures as described in EXAMPLE 8 and starting with 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and (R)-tert-butyl 2-ethylpiperazine-1-carboxylate, 142 was obtained as an off-white solid (12.7 mg, 10%) over 2 steps. 1H NMR (400 MHz, DMSO) δ 9.18-9.06 (s, 1H), 8.67-8.59 (s, 1H), 8.56-8.49 (s, 1H), 8.31-8.25 (s, 1H), 7.95-7.90 (s, 1H), 7.78-7.70 (t, J=8.1 Hz, 1H), 7.23-7.15 (d, J=7.7 Hz, 1H), 6.84-6.76 (d, J=8.5 Hz, 1H), 4.27-4.15 (m, 4H), 3.10-3.03 (d, J=11.7 Hz, 1H), 3.01-2.93 (td, J=11.8, 3.0 Hz, 1H), 2.86-2.77 (td, J=11.6, 3.0 Hz, 1H), 2.68-2.56 (m, 2H), 1.48-1.38 (m, 5H), 0.94-0.87 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 403.2 [M+H]+

出典と根拠

ORDレコード
ord-0f273897961e443f9a52390daa1e4674
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

関連ノート

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