Methanol → HCID 58001327, compound

HRID 1945448Notes

Reaction equation

HRID 1945448 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12]([OH:14])=O)=[O:7].[CH2:23]([NH2:29])[C:24]1[O:28][CH:27]=[CH:26][CH:25]=1.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>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12]([NH:29][CH2:23][C:24]1[O:28][CH:27]=[CH:26][CH:25]=1)=[O:14])=[O:7]

Participants

7

Reactant 4

HCID 887MethanolHCID 3438FurfurylamineHCID 2724699PyBOPHCID 580013332-[2-(2,4-Dichloro-phenoxy)acetylamino]-isonicotinic acid

Product 1

HCID 58001327HCID 58001327, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To solution of 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-isonicotinic acid (16 mg, 0.047 mmol), furfuryl amine (9.1 mg, 0.094 mmol) and DMAP (8.6 mg, 0.07 mmol) in DMF 4 ml was added PyBOP (36 mg, 0.07 mmol) at room temperature, and stirred. 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 resultant crude product was purified by PLC (MeOH:MC=1:9) to afford 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-furan-2-ylmethyl-isonicotinamide as a colorless solid (5 mg, 25.3% 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 resultant crude product was purified by PLC (MeOH:MC=1:9)

Sources & evidence

ORD record
ord-f8db4051a15b410f91bcbbdd22fc79c1
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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