Phosphoric Acid → HCID 178518347, compound

HRID 2236800Notes

Reaction equation

HRID 2236800 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.P(=O)(O)(O)O>CN(C)C=O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 178452239HCID 178452239, compound

Product 1

HCID 178518347HCID 178518347, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A N,N-dimethylformamide mixture (0.6 mL) of tert-butyl 4-(4-{[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}phenyl)piperazine-1-carboxylate (50 mg, 0.087 mmol) and concentrated phosphoric acid (0.6 mL) is heated at 60 C for 2 h. After evaporating to dryness, the residue is partitioned between methylene chloride and saturated sodium bicarbonate. The organic layer is washed with water, dried, and evaporated to yield 10 mg (24%) of the title compound as an orange solid. MS (ESI) m/z 475.2 (M+H)+1

Workup

  1. customAfter evaporating to dryness
  2. customthe residue is partitioned between methylene chloride and saturated sodium bicarbonate
  3. washThe organic layer is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-216c8b4dbb024ab2a5582657fd9dcd00
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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