6-(Piperazin-1-yl)pyridine-3-carbonitrile → 6-(4-(3-(5-(2,2,2-Trifluoroacetyl)thiophen-2-yl)benzoyl)piperazin-1-yl)nicotinonitrile

HRID 874976Notes

Reaction equation

HRID 874976 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:15][C:16]([F:34])([F:33])[C:17]([C:19]1[S:23][C:22]([C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27](O)=[O:28])=[CH:21][CH:20]=1)=[O:18]>C(O)=O>[F:34][C:16]([F:15])([F:33])[C:17]([C:19]1[S:23][C:22]([C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][N:8]=3)[CH2:6][CH2:5]2)=[O:28])=[CH:21][CH:20]=1)=[O:18]

Participants

4

Reactant 2

HCID 27371846-(Piperazin-1-yl)pyridine-3-carbonitrileHCID 248966243-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic Acid

Product 1

HCID 533278596-(4-(3-(5-(2,2,2-Trifluoroacetyl)thiophen-2-yl)benzoyl)piperazin-1-yl)nicotinonitrileYield 32%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

This compound was synthesized from 6-(piperazin-1-yl)nicotinonitrile and 3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzoic acid as described for example 37 step 3 (60 mg, yield 32%). 1H NMR (400 MHz, DMSO-d6) δ 8.52 (d, J=2.1 Hz, 1H), 8.19-8.17 (dd, J=4.0 Hz, J=1.5 Hz, 1H), 8.00-7.89 (m, 4H), 7.64-7.61 (m, 1H), 7.57-7.55 (m, 1H), 6.96-6.94 (t, J=9.2 Hz, 1H), 3.82-3.74 (m, 6H), 3.47 (m, 2H). MS (ESI) m/z: Calculated for C23H17F3N4O2S: 470.10. found: 515.6 (M+HCOOH)−

Sources & evidence

ORD record
ord-f2284173873a4381826bb57d555c1e9c
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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