4-Cyano-2,2-dimethylbutanoic acid → 6-(4-(4-Cyano-2,2-dimethylbutanoyl)-3-methylpiperazin-1-yl)nicotinonitrile

HRID 874979Notes

Reaction equation

HRID 874979 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][C:20]([CH3:25])([CH3:24])[C:21](O)=[O:22])#[N:17]>>[C:16]([CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[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 2456284-Cyano-2,2-dimethylbutanoic acidHCID 624798016-(3-Methylpiperazin-1-yl)nicotinonitrile

Product 1

HCID 673235386-(4-(4-Cyano-2,2-dimethylbutanoyl)-3-methylpiperazin-1-yl)nicotinonitrileYield 17%

Procedure

This compound was synthesized from 6-(3-methylpiperazin-1-yl)nicotinonitrile and 4-cyano-2,2-dimethylbutanoic acid as described for example 37 step 3 (400 mg, yield 17%) as yellow viscous liquid. 1H NMR (300 MHz, MeOD) δ 8.40-8.39 (dd, J=2.2 Hz, 0.7 Hz, 1H), 7.76-7.72 (dd, J=9.1 Hz, 2.3 Hz, 1H), 6.86-6.83 (d, J=9.0 Hz, 1H), 4.69-4.65 (m, 1H), 4.32-4.22 (m, 3H), 3.41-3.35 (m, 2H), 3.20-3.14 (m, 1H), 2.50-2.45 (m, 2H), 2.04-1.95 (m, 2H), 1.33 (s, 6H), 1.20-1.18 (m, 3H). MS (ESI) m/z: Calculated for C18H23N5O: 325.19. found: 326.1 (M+H)+

Sources & evidence

ORD record
ord-9c815e819bc946208197cfea2a529ddf
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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