6-(3-Methylpiperazin-1-yl)nicotinonitrile → 6-(3-Methyl-4-(4-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)butanoyl)piperazin-1-yl)nicotinonitrile

HRID 874991Notes

Reaction equation

HRID 874991 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.[F:16][C:17]([F:32])([F:31])[C:18]([C:20]1[S:24][C:23]([CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])=[CH:22][CH:21]=1)=[O:19]>>[CH3:1][CH:2]1[N:7]([C:28](=[O:29])[CH2:27][CH2:26][CH2:25][C:23]2[S:24][C:20]([C:18](=[O:19])[C:17]([F:31])([F:32])[F:16])=[CH:21][CH:22]=2)[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

Participants

3

Reactant 2

HCID 624798016-(3-Methylpiperazin-1-yl)nicotinonitrileHCID 673230854-(5-(2,2,2-Trifluoroacetyl)thiophen-2-yl)butanoic acid

Product 1

HCID 533278836-(3-Methyl-4-(4-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)butanoyl)piperazin-1-yl)nicotinonitrileYield 16%

Procedure

This compound was synthesized from 6-(3-methylpiperazin-1-yl)nicotinonitrile and 4-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)butanoic acid as described for example 37 step 3 (40 mg, yield 16%). 1H NMR (400 MHz, DMSO-d6, 80° C.) δ 8.45-8.44 (m, 1H), 7.98-7.96 (m, 1H), 7.82-7.79 (dd, J=9.1 Hz, 2.4 Hz, 1H), 7.20-7.19 (d, J=4.0 Hz, 1H), 6.89-6.87 (d, J=9.1 Hz, 1H), 4.45 (m, 1H), 4.20-4.14 (m, 2H), 3.98 (m, 1H), 3.39-3.34 (dd, J=13.4 Hz, 4.0 Hz, 1H), 3.27 (m, 1H), 3.17-3.11 (m, 1H), 2.99 (m, 1H), 2.89 (m, 1H), 2.46-2.36 (m, 2H), 2.01-1.94 (m, 2H), 1.11-1.09 (d, J=6.7 Hz, 3H). MS (ESI) m/z: Calculated for C21H21F3N4O2S: 450.13. found: 449.2 (M−H)−

Sources & evidence

ORD record
ord-2f26ab33a8cd4f87b0179444cf02d210
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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