HCID 21092639, compound → HCID 21092647, compound

HRID 1348932Notes

Reaction equation

HRID 1348932 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:14]4[C:15]5[CH:16]=[C:17]([N+:23]([O-])=O)[CH:18]=[CH:19][C:20]=5[O:21][CH2:22][C:13]=4[C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1>[Ni].CN(C=O)C>[NH2:23][C:17]1[CH:18]=[CH:19][C:20]2[O:21][CH2:22][C:13]3[C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:11][N:10]([C:8]4[CH:7]=[CH:6][C:5]5[O:1][CH2:2][O:3][C:4]=5[CH:9]=4)[C:14]=3[C:15]=2[CH:16]=1

Participants

4

Reactant 1

HCID 21092639HCID 21092639, compound

Product 1

HCID 21092647HCID 21092647, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

The title material from step 3 (17 g, 0.0416 mol) was treated with Raney nickel in DMF under 25 psi at RT for 17 h. The reaction mixture was filtrated and washed with DMF. The combined filtrate and washes were concentrated under reduced pressure. The resulting residue was diluted with MeOH, sonicated at 40° C., the solid was collected by filtration, to give ethyl 8-amino-1-[1,3-benzodioxol-5-yl]-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxylate (12.3415 g, 78.3%). The product was characterized by 1H NMR, LC/MS (MH+ 380), and HPLC (98% purity).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. washwashed with DMF
  3. concentrationThe combined filtrate and washes were concentrated under reduced pressure
  4. additionThe resulting residue was diluted with MeOH
  5. customsonicated at 40° C.
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-243caf65b3e141599950f874e8397dce
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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