3-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic Acid → 6-(3-Methyl-4-(3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzoyl)piperazin-1-yl)nicotinonitrile

HRID 874975Notes

Reaction equation

HRID 874975 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:35])([F:34])[C:18]([C:20]1[S:24][C:23]([C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28](O)=[O:29])=[CH:22][CH:21]=1)=[O:19]>C(O)=O>[CH3:1][CH:2]1[N:7]([C:28](=[O:29])[C:27]2[CH:31]=[CH:32][CH:33]=[C:25]([C:23]3[S:24][C:20]([C:18](=[O:19])[C:17]([F:16])([F:34])[F:35])=[CH:21][CH:22]=3)[CH:26]=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

4

Reactant 2

HCID 248966243-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic AcidHCID 624798016-(3-Methylpiperazin-1-yl)nicotinonitrile

Product 1

HCID 533278586-(3-Methyl-4-(3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzoyl)piperazin-1-yl)nicotinonitrileYield 39%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

This compound was synthesized from 6-(3-methylpiperazin-1-yl)nicotinonitrile and 3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzoic acid as described for example 37 step 3 (95 mg, yield 39%). 1H NMR (400 MHz, MeOD) δ 8.42 (d, J=1.9 Hz, 1H), 7.97-7.96 (m, 1H), 7.80-7.77 (dt, J=7.8 Hz, 1.4 Hz, 1H), 7.75-7.74 (t, J=1.5 Hz, 1H), 7.68-7.65 (dd, J=9.1 Hz, 2.4 Hz, 1H), 7.58-7.54 (t, J=7.6 Hz, 1H), 7.48-7.45 (m, 2H), 6.64-6.62 (d, J=9.1 Hz, 1H), 4.40-4.23 (m, 4H), 3.42-3.37 (m, 2H), 3.16-3.09 (m, 1H), 1.33-1.31 (m, 3H). MS (ESI) m/z: Calculated for C24H19F3N4O2S: 484.12. found: 529.7 (M+HCOOH)−

Sources & evidence

ORD record
ord-b412be574c1842dbbc103cc81a25e5c1
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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