Sodium hydride → HCID 22478542, compound

HRID 2416603Notes

Reaction equation

CC(O)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]2)[CH:8]=[N:9][CH:10]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[C:4]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]2)[CH:8]=[N:9][CH:10]=1)#[CH:3]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-[5-(3-methyl-3-hydroxy-butyn-1-yl)-3-pyridyl]-4-tert-butoxycarbonyl-homopiperazine (0.40 g, 1.1 mmol), sodium hydride 60% (4.5 mg, 0.11 mmol) and toluene (10 ml) was stirred at 110° C. for 3 h. The crude mixture was purified by chromatography on silica gel with ethyl acetate:toluene, (3:1) gave the title compound. Yield 0.13 g, 39%.

Workup

customThe crude mixture was purified by chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record: ord-fff4391c742247e98c5a91ca69ad053f
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825189B1

Reaction notes

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