Dimethylformamide → 2-[2-(4-Tert-butyl-phenoxy)-acetylamino]-isonicotinic acid methyl ester

HRID 1945434Notes

Reaction equation

[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].NC1C=[C:19](C=CN=1)[C:20](N)=[O:21].CC[N:28]([CH:32]([CH3:34])C)[CH:29]([CH3:31])C.C1C[N:38]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CN([CH:71]=[O:72])C>>[CH3:71][O:72][C:20](=[O:21])[C:19]1[CH:31]=[CH:29][N:28]=[C:32]([NH:38][C:11](=[O:13])[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:15][CH:14]=2)[CH:34]=1

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 157182-(4-Tert-butylphenoxy)acetic acid

HCID 81531Diisopropylethylamine

HCID 3516532-Aminoisonicotinamide

HCID 2724699PyBOP

Product 1

HCID 248120972-[2-(4-Tert-butyl-phenoxy)-acetylamino]-isonicotinic acid methyl esterYield 50.3%

Procedure

A solution of (4-tert-butyl-phenoxy)acetic acid (200.1 mg, 0.96 mmol), 2-amino-isonicotinamide (109.5 mg, 0.72 mmol), DIPEA (0.17 ml, 0.96 mmol) and PyBOP (499.5 mg, 0.96 mmol) in DMF 6.0 mL was stirred, then partitioned between ethyl acetate and water. The organic phase was purified by preparative TLC(Hexane:EtoAC:MeOH=15:3:1) to give 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a white solid (124.0 mg, 50.3% yield).

Workup

custompartitioned between ethyl acetate and water
customThe organic phase was purified by preparative TLC(Hexane:EtoAC:MeOH=15:3:1)

Sources & evidence

ORD record: ord-36b99e1d20c54840a42e6cbee3b2a6b5
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394799B2

Reaction notes

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