2-Bromo-6-fluoropyridine → (R)-1-(6-(6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepan-6-ol

HRID 57943

反応式

HRID 57943 の反応式
[NH:1]1[CH2:7][CH:6]([OH:8])[CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[C:12](F)[N:11]=1.Cl[C:18]1[N:23]=[CH:22][C:21]2[CH:24]=[N:25][NH:26][C:20]=2[CH:19]=1.[CH3:27][N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1>>[CH3:27][N:28]1[CH:32]=[C:31]([C:18]2[N:23]=[CH:22][C:21]3[CH:24]=[N:25][N:26]([C:12]4[N:11]=[C:10]([N:1]5[CH2:7][C@H:6]([OH:8])[CH2:5][NH:4][CH2:3][CH2:2]5)[CH:15]=[CH:14][CH:13]=4)[C:20]=3[CH:19]=2)[CH:30]=[N:29]1

参加物

5

反応物 4

HCID 6394382-Bromo-6-fluoropyridineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 211142751,4-Diazepan-6-olHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

生成物 1

HCID 86707128(R)-1-(6-(6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepan-6-ol収率 24.1%

実験手順

Following the procedures as described in Example 124 and starting with 1,4-diazepan-6-ol, 2-bromo-6-fluoropyridine, 6-chloro-1H-pyrazolo[4,3-c]pyridine, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 229 was obtained as a yellow solid (40 mg, 24.1%) over six steps. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.09 (s, 1H), 8.65 (s, 1H), 8.44 (s, 1H), 8.25 (s, 1H), 7.98 (s, 1H), 7.63-7.68 (m, 1H), 7.14-7.16 (d, J=12.5 Hz, 1H), 6.61-6.64 (d, J=14 Hz, 1H), 4.10-4.14 (m, 1H), 3.86-3.91 (m, 6H), 3.55-3.66 (m, 2H), 2.98-3.04 (m, 3H), 2.84-2.90 (m, 1H), 2.69-2.71 (m, 1H); MS (ESI) m/z: 391 [M+H]+.

出典と根拠

ORDレコード
ord-bc9c6952d7d046b8a48fb5195c6b113b
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

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