Methanol → Isonicotinamide

HRID 1945460Notes

Reaction equation

HRID 1945460 reaction equation
O(CC(O)=O)C1C=CC=CC=1.N[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][N:21]=1)[C:16]([NH2:18])=[O:17].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>[C:16]([NH2:18])(=[O:17])[C:15]1[CH:19]=[CH:20][N:21]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 19188Phenoxyacetic AcidHCID 3516532-AminoisonicotinamideHCID 2724699PyBOP

Product 1

HCID 15074IsonicotinamideYield 65.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To solution of (phenoxy-acetic acid (100 mg, 0.65 mmol), 2-amino isonicotinamide (180 mg, 1.31 mmol) and DMAP (160 mg, 1.31 mmol) in DMF 5 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-Hexanes:MeOH=1:2:1˜1:2:2) to afford 242-phenoxy-acetylamino)-isonicotinamide as a colorless solid (0.105 g, 58.9% 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-Hexanes:MeOH=1:2:1˜1:2:2)

Sources & evidence

ORD record
ord-d555f07797604397abdab23c4acc8cf3
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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