4-Cyanobutanoic acid → 6-(4-(4-Cyanobutanoyl)-3-methylpiperazin-1-yl)nicotinonitrile

HRID 874957Notes

Reaction equation

HRID 874957 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:3]1.[C:16]([CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])#[N:17]>>[C:16]([CH2:18][CH2:19][CH2:20][C:21]([N:7]1[CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:3][CH:2]1[CH3:1])=[O:22])#[N:17]

Participants

3

Reactant 2

HCID 382394-Cyanobutanoic acidHCID 624798016-(3-Methylpiperazin-1-yl)nicotinonitrile

Product 1

HCID 673254606-(4-(4-Cyanobutanoyl)-3-methylpiperazin-1-yl)nicotinonitrileYield 85%

Procedure

This compound was synthesized from 6-(3-methylpiperazin-1-yl)nicotinonitrile and 4-cyanobutyric acid as described for example 37 step 3 (900 mg, yield 85%) and it was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 8.41-8.40 (dd, J=2.3 Hz, 0.5 Hz, 1H), 7.67-7.63 (dd, J=9.0 Hz, 2.2 Hz, 1H), 6.61-6.58 (d, J=9.0 Hz, 1H), 4.46-4.19 (m, 4H), 3.54-3.36 (m, 2H), 3.16-3.11 (m, 2H), 2.59-2.51 (m, 3H), 2.06-2.01 (m, 2H), 1.26 (m, 3H). MS (ESI) m/z: Calculated for C16H19N6O: 297.16. found: 298.0 (M+H)+

Workup

  1. customwas carried through without further purification

Sources & evidence

ORD record
ord-837d4ce2a0724fd19f6ab1bcef5eed92
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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