Cyclopropylboronic acid → 1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(1-cyclopropyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57880Notes

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.[CH:35]1(B(O)O)[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:5]=[N:1][N:2]([CH:35]6[CH2:37][CH2:36]6)[CH:3]=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 2760897Cyclopropylboronic acid

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 727155401-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(1-cyclopropyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 25%

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 cyclopropylboronic acid, 174 was obtained as a yellow solid (40 mg, 25%) over two steps. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.13 (s, 1H), 8.64 (s, 1H), 8.52 (s, 1H), 8.26 (s, 1H), 7.98 (s, 1H), 7.66-7.70 (t, J=16 Hz, 1H), 7.14-7.17 (t, J=14.5 Hz, 1H), 6.58-6.66 (m, 1H), 6.06-6.12 (m, 1H), 5.21-5.28 (m, 2H), 4.84-4.85 (d, J=10 Hz, 2H), 3.35-3.90 (m, 7H), 2.97-2.99 (t, J=10.5 Hz, 1H), 2.71-2.73 (t, J=12 Hz, 1H), 1.87-1.89 (t, J=10 Hz, 2H); MS (ESI) m/z: 401 [M+H]+.

Sources & evidence

ORD record: ord-b09ecf58eaf049d592c7b1b52227736f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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