Ammonia → HCID 18444277, compound

HRID 459864Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)=[O:18])[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1N=C[N:36](C(N2C=NC=C2)=O)C=1.N>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]([N:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:26]=[CH:27][C:28]([C:29]([NH2:36])=[O:31])=[CH:32][CH:33]=4)[CH2:23][CH2:24]3)=[O:18])[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

To a THF (5 ml) solution of 171 mg of 4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}benzoic acid was added 63 mg of CDI, followed by stirring at 60° C. Further, 52 mg of CDI was added in twice thereto, and the whole was stirred at 60° C. for 24 hours in total. After the reaction solution was cooled to room temperature, 0.25 ml of aqueous ammonia was added thereto, followed by 6 hours of stirring at room temperature. Further, 0.5 ml of aqueous ammonia was added thereto and the whole was stirred at room temperature. Thus precipitated crude crystals were collected by filtration and recrystallized from methanol-THF to obtain 68 mg of 4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}benzamide as colorless crystals.

Workup

stirringwas stirred at 60° C. for 24 hours in total
temperatureAfter the reaction solution was cooled to room temperature
stirringof stirring at room temperature
stirringthe whole was stirred at room temperature
customThus precipitated crude crystals
filtrationwere collected by filtration
customrecrystallized from methanol-THF

Sources & evidence

ORD record: ord-eb522da1f1d3484fae47bafe1ca45ae4
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196080B2

Reaction notes

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