1-(3-Methyl-2-pyridinyl)piperazine → 2-{[4-(3-Methyl-2-pyridinyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine

HRID 1828294Notes

Reaction equation

HRID 1828294 reaction equation
[CH3:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O[BH-](O[C:24](=[O:26])[CH3:25])OC(=O)C)(=O)C.[Na+]>>[CH3:1][C:2]1[C:3]([N:8]2[CH2:9][CH2:10][N:11]([CH2:7][C:6]3[O:26][C:24]4[C:25](=[N:4][CH:3]=[CH:2][CH:1]=4)[CH:5]=3)[CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27600571-(3-Methyl-2-pyridinyl)piperazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 98614252-{[4-(3-Methyl-2-pyridinyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine

Procedure

The product from Example 35B, 1-(3-methyl-2-pyridinyl)piperazine, and sodium triacetoxyborohydride were processed as described in Example 35C to provide the title compound. 1H NMR (CDCl3, 300 MHz) 62.68 (m, 4H), 3.29 (s, 3H), 3.58 (m, 4H), 3.79 (s, 2H), 6.41 (d, J=8.48 Hz, 1H), 6.49 (d, J=7.12 Hz, 1H), 6.85 (s, 1H), 7.18 dd, J=4.75, 8.14 Hz, 1H), 7.36 (dd, J=7.12, 8.14 Hz, 1H), 7.73 (dd, J=1.02, 8.14 Hz, 1H), 8.51 (dd, J=1.36, 4.75 Hz, 1H); MS (DCI/NH3) m/z 309.2 (M+H)+.

Sources & evidence

ORD record
ord-0669a961823941a6a897f16dc1efa5ec
Source dataset
uspto-grants-2006_06
Patent number
US07057042B2

Reaction notes

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