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

HRID 1945434
Notes
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Reaction equation

HRID 1945434 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 157182-(4-Tert-butylphenoxy)acetic acidHCID 81531DiisopropylethylamineHCID 3516532-AminoisonicotinamideHCID 2724699PyBOP

Product 1

HCID 248120972-[2-(4-Tert-butyl-phenoxy)-acetylamino]-isonicotinic acid methyl ester
Yield 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

  1. custompartitioned between ethyl acetate and water
  2. 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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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes