Methanol → HCID 58001330, compound

HRID 1945461Notes

Reaction equation

HRID 1945461 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19]([NH2:21])=[O:20].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CO>CN(C1C=CN=CC=1)C.CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([NH:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=2)[C:19]([NH2:21])=[O:20])=[O:12])=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 15720(4-Nitrophenoxy)acetic acidHCID 3516532-AminoisonicotinamideHCID 2724699PyBOP

Product 1

HCID 58001330HCID 58001330, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To solution of (4-nitro-phenoxy)-acetic acid (50 mg, 0.25 mmol), 2-amino isonicotinamide (52 mg, 0.37 mmol) and DMAP (62 mg, 0.5 mmol) in DMF 6 ml was added PyBOP (684 mg, 1.31 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by PLC (EtOAc:n-Hexane:MeOH=1:2:1˜1:2:2) to afford 2-[2-(4-nitro-phenoxy)-acetylamino]-isonicotinamide as a colorless solid (0.04 g, 50% yield).

Workup

  1. customReaction mixture
  2. additionwas poured onto ice cold water
  3. customThe organic phase was separated
  4. washsequentially washed with aqueous sodium bicarbonate, brine and water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by PLC (EtOAc:n-Hexane:MeOH=1:2:1˜1:2:2)

Sources & evidence

ORD record
ord-e5bd852248aa4b7999967fb69473e34d
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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