1-Ethylpiperazine → HCID 117600414, compound

HRID 526584Notes

Reaction equation

HRID 526584 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][N:17]=3)[C:13]=2[O:14][CH3:15])=[C:5]([CH3:25])[C:4]=1[F:26])#[N:2].C1C=C2N=NN(O)C2=CC=1.O.Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)C(C)C)C.[CH2:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)[CH3:60]>CN(C=O)C>[CH2:59]([N:61]1[CH2:66][CH2:65][N:64]([C:20]([C:19]2[CH:23]=[CH:24][C:16]([N:12]3[C:13]([O:14][CH3:15])=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:26])[C:5]=4[CH3:25])[CH:10]=[N:11]3)=[N:17][CH:18]=2)=[O:22])[CH2:63][CH2:62]1)[CH3:60]

Participants

7

Reactant 5

HCID 791961-EthylpiperazineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 1176003206-(4-(4-cyano-3-fluoro-2-methylphenyl)-5-methoxy-1H-pyrazol-1-yl)nicotinic acid

Product 1

HCID 117600414HCID 117600414, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combined 6-(4-(4-cyano-3-fluoro-2-methylphenyl)-5-methoxy-1H-pyrazol-1-yl)nicotinic acid (106 mg, 0.300 mmol), HOBT hydrate (68.9 mg, 0.450 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (86 mg, 0.450 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.157 mL) in DMF (1 mL) and stirred for 5 min. The mixture was then added to 1-ethylpiperazine (68.5, 0.600 mmol). After 18 hours the reaction mixture was purified via preparative HPLC (20-40% acetonitrile in water, with TFA) to give 4-(1-(5-(4-ethylpiperazine-1-carbonyl)pyridin-2-yl)-5-methoxy-1H-pyrazol-4-yl)-2-fluoro-3-methylbenzonitrile (70 mg, 0.156 mmol, 52%). ESI-MS m/z [M+H]+ 449.3.

Workup

  1. customAfter 18 hours the reaction mixture was purified via preparative HPLC (20-40% acetonitrile in water, with TFA)

Sources & evidence

ORD record
ord-9c55314932fc4e03bc1172ccf12e2b3e
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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