HCID 11091112, compound → 3H-1,2,4-Triazol-3-one, 2-(1-ethylpropyl)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-

HRID 527183Notes

Reaction equation

HRID 527183 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:25](=[O:26])[N:24]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[N:23]=[CH:22]4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1>Br>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:16]=[CH:17][C:18]([N:21]4[C:25](=[O:26])[N:24]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[N:23]=[CH:22]4)=[CH:19][CH:20]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 11091112HCID 11091112, compound

Product 1

HCID 712957103H-1,2,4-Triazol-3-one, 2-(1-ethylpropyl)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-Yield 98%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

This compound was synthesized as a white amorphous solid from 4j (41.5 mg, 0.099 mmol) in 48% aqueous HBr (1.0 mL) in 98% yield by following general procedure 1.4: 1H NMR (400 MHz, CDCl3, δH) 7.64 (s, 1H), 7.40 (d, J=8.9 Hz, 2H), 7.04-6.92 (m, 4H), 6.72 (d, J=8.5 Hz, 2H), 4.15-3.97 (m, 1H), 3.42-3.31 (m, 4H), 3.29-3.18 (m, 4H), 1.95-1.62 (m, 4H), 0.89 (t, J=7.4 Hz, 6H); 13C NMR (100 MHz, CDCl3, δC) 153.31, 151.93, 150.78, 143.66, 134.54, 125.92, 124.36, 119.46, 116.94, 116.36, 59.27, 51.82, 49.09, 26.99, 10.97. MALDI-MS: 408.2 (M+H+), 430.2 (M+Na+).

Sources & evidence

ORD record
ord-96d93df78fd04983be1b45e8e1138c58
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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