Methanol → HCID 58001329, compound

HRID 1945453Notes

Reaction equation

HRID 1945453 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:13][C:14]1[N:22]=[CH:21][CH:20]=[CH:19][C:15]=1C(N)=O.C1CN([P+](ON2N=[N:47][C:42]3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C[OH:57]>CN(C1C=CN=CC=1)C.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:13][C:14]2[CH:15]=[C:19]([CH:20]=[CH:21][N:22]=2)[C:42]([NH2:47])=[O:57])=[O:10])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 678824-Fluorophenoxyacetic acidHCID 5066232-Aminopyridine-3-carboxamideHCID 2724699PyBOP

Product 1

HCID 58001329HCID 58001329, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To solution of (4-fluoro-phenoxy)-acetic acid (100 mg, 0.43 mmol), 2-amino nicotinamide (89.39 mg, 0.65 mmol) and DMAP (106 mg, 0.86 mmol) in DMF 5 ml was added PyBOP (452 mg, 0.86 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:Hexaane:MeOH=3:6:1-2:4:1) to afford 2-[2-(4-fluoro-phenoxy)-acetylamino]-isonicotinamide as a colorless solid (0.08 g, 59% 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:Hexaane:MeOH=3:6:1-2:4:1)

Sources & evidence

ORD record
ord-b9d385603ef5422cb9ce327fe3a6e591
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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