(3R)-3-Aminopiperidine, 3-BOC protected → (R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amine

HRID 1775091Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11](COCC[Si](C)(C)C)[N:10]=2)=[N:6][C:7]=1F.[NH:32]1[CH2:37][CH2:36][CH2:35][C@@H:34]([NH:38]C(=O)OC(C)(C)C)[CH2:33]1>>[Br:1][C:2]1[C:7]([N:32]2[CH2:37][CH2:36][CH2:35][C@@H:34]([NH2:38])[CH2:33]2)=[N:6][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[NH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 1514172(3R)-3-Aminopiperidine, 3-BOC protected

HCID 71253450HCID 71253450, compound

Product 1

HCID 71253934(R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-amineYield 35.9%

Procedure

Following the procedures as described in Example 241 and starting with 3-(5-bromo-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine and (R)-tert-butyl piperidin-3-ylcarbamate, 290 was obtained as an off-white solid (19.7 mg, 35.9%) over two steps. 1H NMR (400 MHz, DMSO) δ 9.31 (s, 1H), 9.22 (s, 1H), 9.03 (s, 1H), 8.59 (d, J=4.7 Hz, 1H), 8.46 (d, J=8.0 Hz, 1H), 8.05 (d, J=8.1 Hz, 1H), 7.70 (d, J=8.1 Hz, 1H), 7.62 (dd, J=11.8, 7.1 Hz, 1H), 7.54 (ddd, J=12.7, 7.2, 4.0 Hz, 2H), 3.92 (d, J=9.3 Hz, 1H), 3.84 (d, J=12.1 Hz, 1H), 2.88 (d, J=12.9 Hz, 2H), 2.81-2.69 (m, 1H), 1.95 (d, J=12.6 Hz, 1H), 1.90-1.69 (m, 2H), 1.26 (dd, J=22.3, 7.8 Hz, 1H); ESI MS m/z=450.1 (M+1)

Sources & evidence

ORD record: ord-f428fa8a5f9046e489f01384f8c07297
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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