Formaldehyde → 2-[4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-piperazinyl]nicotinonitrile

HRID 1828287Notes

Reaction equation

HRID 1828287 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[N:10]1([C:16]2[N:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:24]([O-])(=O)C.[Na+].C=O>>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:24][N:13]2[CH2:12][CH2:11][N:10]([C:16]3[N:23]=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])[CH2:15][CH2:14]2)=[CH:2]1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 517045Sodium AcetateHCID 27372032-(Piperazin-1-yl)pyridine-3-carbonitrile

Product 1

HCID 220659942-[4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-piperazinyl]nicotinonitrile

Procedure

1H-pyrrolo[2,3-b]pyridine (47 mg, 0.40 mmol), 2-(1-piperazinyl)nicotinonitrile (75 mg, 0.48 mmol), sodium acetate (72 mg, 0.53 mmol), and formaldehyde (0.48 mmol) were processed as described in Example 18 to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.57 (m, 4H) 3.50 (m, 4H) 3.84 (s, 2H) 6.63 (m, 2H) 6.81 (m, 1H) 7.32 (m, 1H) 7.52 (m, 1H) 7.77 (m, 1H) 7.90 (m, 1H). (ESI) m/z 319 (M+H)+.

Sources & evidence

ORD record
ord-b139c597029b49bd9dfc1b67b891aac2
Source dataset
uspto-grants-2006_06
Patent number
US07057042B2

Reaction notes

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