1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 3-(6-Hydroxy-1,4-diazepan-1-yl)-1-methyl-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyrazin-2(1H)-one

HRID 57974Notes

Reaction equation

HRID 57974 reaction equation
[NH:1]1[CH2:7][CH:6]([OH:8])[CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:10]1[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=[C:14](Br)[N:15]=1.Cl[C:20]1[N:25]=[CH:24][C:23]2[CH:26]=[N:27][NH:28][C:22]=2[CH:21]=1.[CH3:29][N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1>>[OH:8][CH:6]1[CH2:5][N:4]([C:10]2[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=[C:14]([N:28]3[C:22]4[CH:21]=[C:20]([C:33]5[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=5)[N:25]=[CH:24][C:23]=4[CH:26]=[N:27]3)[N:15]=2)[CH2:3][CH2:2][NH:1][CH2:7]1

Participants

5

Reactant 4

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 211142751,4-Diazepan-6-olHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

Product 1

HCID 867071563-(6-Hydroxy-1,4-diazepan-1-yl)-1-methyl-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyrazin-2(1H)-oneYield 7.2%

Procedure

Following the procedures as described in Example 124 and starting with 1,4-diazepan-6-ol, 3,5-dibromo-1-methylpyrazin-2(1H)-one, 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, 254 was obtained as a yellow solid (80 mg, 7.2%) over five steps. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.09 (s, 1H), 8.43 (s, 1H), 8.30 (s, 1H), 8.29 (s, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 4.91 (s, 1H), 4.49 (m, 1H), 3.92 (m, 1H), 3.89 (s, 3H), 3.70-3.71 (m, 2H), 3.51 (s, 3H), 2.99-3.02 (m, 1H), 2.90-2.91 (m, 1H), 2.74-2.86 (m, 2H); MS (ESI) m/z: 422 [M+H]+.

Sources & evidence

ORD record
ord-7433d3c2b28442f69cffb0e1ccadbe21
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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