Acetyl chloride → N-[3-(4-{2-[4-(cyclohexylmethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]ethyl}piperazin-1-yl)phenyl]acetamide

HRID 1514172Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[N:17]([CH2:22][CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[C:18](=[O:21])[NH:19][N:20]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:29](Cl)(=[O:31])[CH3:30]>N1C=CC=CC=1>[CH:23]1([CH2:22][N:17]2[C:18](=[O:21])[NH:19][N:20]=[C:16]2[CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:4]3[CH:3]=[C:2]([NH:1][C:29](=[O:31])[CH3:30])[CH:7]=[CH:6][CH:5]=3)[CH2:13][CH2:12]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-{2-[4-(3-aminophenyl)piperazin-1-yl]ethyl}-4-(cyclohexylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one D10 (0.13 g, 0.34 mmol) in pyridine (2 mL) was cooled to 0° C. and acetyl chloride (0.025 mL, 0.029 g, 0.36 mmol) was added. The reaction mixture was stirred at 0° C. for 18 hrs and then evaporated to dryness. The residue was purified by flash chromatography (Silica gel 60 Å, 45 μm, 10% methanol in dichloromethane) and afforded 0.015 g (10%) N-[3-(4-{2-[4-(cyclohexylmethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]ethyl}piperazin-1-yl)phenyl]acetamide E38 as an orange oil.

Workup

customevaporated to dryness
customThe residue was purified by flash chromatography (Silica gel 60 Å, 45 μm, 10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-995e8bb6f936413e8715fc8cca19b5e4
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222254B2

Reaction notes

Loading…