Bromoacetonitrile → 2-(4-(1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-1H-pyrazol-1-yl)acetonitrile

HRID 57855Notes

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.Br[CH2:36][C:37]#[N:38]>>[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]([CH2:36][C:37]#[N:38])[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 11534Bromoacetonitrile

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 867070532-(4-(1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-1H-pyrazol-1-yl)acetonitrileYield 18.5%

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 2-bromoacetonitrile, 155 was obtained as a white solid (25 mg, 18.5%) over two steps. 1H NMR (500 MHz, CDCl3) δ (ppm) 9.064-9.065 (d, J=0.5 Hz, 1H), 8.75 (s, 1H), 8.25 (s, 1H), 8.19 (s, 1H), 8.05 (s, 1H), 7.61-7.64 (t, J=16.5 Hz, 1H), 7.28 (s, 1H), 6.43-6.45 (d, J=8.5 Hz, 1H), 5.15 (s, 2H), 3.88-3.92 (m, 4H), 3.17-3.19 (t, J=11 Hz, 2H), 2.92-2.94 (t, J=11 Hz, 2H), 2.02-2.05 (t, J=12 Hz, 2H); MS (ESI) m/z: 400 [M+H]+.

Sources & evidence

ORD record: ord-30ad4a296f8b45ebac87fcff6006ddd4
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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