HCID 22612140, compound → HCID 22612372, compound

HRID 844061Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C:14]2[C:15]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:29][Li]>O1CCCC1>[C:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[O:20][C:15]1[C:14]([NH:13][C:11](=[O:12])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:29])[CH3:2])=[CH:9][CH:8]=2)=[CH:19][CH:18]=[CH:17][N:16]=1)#[N:28]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-(4-Acetyl-phenyl)-N-[2-(3-cyano-phenoxy)-pyridin-3-yl]-acetamide (0.360 grams, 0.96 mmole) in tetrahydrofuran (15 ml) at −78° C. 1.0 M methyl lithium (2.03 ml, 2.03 mmole) in tetrahydrofuran (20 ml) was added and stirred at −78° C. for 1 hour. The reaction was quenched with water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to give a white solid which was purified by chromatography on silica eluting with 40% ethyl acetate/hexane. Recrystalization from ethyl acetate/hexane gave white crystals (0.115 g). M.P. 97-99° C.; Anal. calcd. for C23H21N3O3: C, 71.30; H, 5.46; N, 10.85. Found: C, 70.96; H, 5.30; N, 10.69.

Workup

customat −78° C
customThe reaction was quenched with water
extractionextracted with ethyl acetate
washThe combined extracts were washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give a white solid which
customwas purified by chromatography on silica eluting with 40% ethyl acetate/hexane
customRecrystalization from ethyl acetate/hexane

Sources & evidence

ORD record: ord-ddb7a8283505480e8fe94fa7f4a1bcea
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380218B1

Reaction notes

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