Methanol → HCID 15342357, compound

HRID 1481317Notes

Reaction equation

HRID 1481317 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[CH3:13]CN=C=NCCCN(C)C.Cl.CO>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:13][O:11][C:10]([C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[O:1][CH:2]=1)=[O:12]

Participants

6

Reactant 3

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 84013601HCID 84013601, compound

Product 1

HCID 15342357HCID 15342357, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of furo[2,3-b]pyridine-3-carboxylic acid (53 mmol) in 85 mL DCM were added EDC.HCl (58 mmol), DMAP (16 mmol) and 4.3 mL MeOH. The beige suspension was stirred at RT for 2 h. The reaction mixture was diluted with 50 mL DCM and quenched with sat. aq. NaHCO3 solution. The organic phase was washed 3 times with sat. aq. NH4Cl solution and once with brine. The organic layer was dried over MgSO4 and concentrated in vacuo to obtain the desired compound as grey solid.

Workup

  1. customquenched with sat. aq. NaHCO3 solution
  2. washThe organic phase was washed 3 times with sat. aq. NH4Cl solution
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32911edd6c3c457aa513a7181ba78bc1
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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