Ethylene Oxide → 2-(4-(1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-1H-pyrazol-1-yl)ethanol

HRID 57852Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]=[CH:10][C:9]3[CH:12]=[N:13][N:14]([C:15]4[N:20]=[C:19]([N:21]5[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]5)[CH:18]=[CH:17][CH:16]=4)[C:8]=3[CH:7]=2)[CH:3]=[N:2]1.[O:35]1[CH2:37][CH2:36]1>>[N:21]1([C:19]2[N:20]=[C:15]([N:14]3[C:8]4[CH:7]=[C:6]([C:4]5[CH:3]=[N:2][N:1]([CH2:37][CH2:36][OH:35])[CH:5]=5)[N:11]=[CH:10][C:9]=4[CH:12]=[N:13]3)[CH:16]=[CH:17][CH:18]=2)[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

Reactant 2

HCID 6354Ethylene Oxide

HCID 86707049tert-butyl 4-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 727153822-(4-(1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-1H-pyrazol-1-yl)ethanolYield 71%

Procedure

Following the procedures as described in Example 61 and starting with tert-butyl 4-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate and oxirane, 152 was obtained as a light yellow solid (102 mg, 71%) over two steps. 1H NMR (500 MHz, CDCl3) δ (ppm) 8.941-8.942 (d, J=0.5 Hz, 1H), 8.57 (s, 1H), 8.17 (s, 1H), 8.07 (s, 1H), 7.86 (s, 1H), 7.57-7.60 (t, J=16 Hz, 1H), 7.22-7.26 (t, J=20.5 Hz, 1H), 6.36-6.37 (d, J=8 Hz, 1H), 4.30-4.32 (t, J=9.5 Hz, 2H), 4.05-4.07 (t, J=9.5 Hz, 2H), 3.77-3.82 (m, 4H), 3.11-3.13 (t, J=10.5 Hz, 2H), 2.88-2.91 (t, J=11.5 Hz, 2H), 2.26 (s, 2H), 1.97-2.01 (m, 2H); MS (ESI) m/z: 405 [M+H]+.

Sources & evidence

ORD record: ord-88face1819424f1e9b2a1d60587430db
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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