Phosphoric Acid → HCID 178518349, compound

HRID 2236818Notes

Reaction equation

HRID 2236818 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:17]=[CH:18][C:19]([N:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)=[N:20][CH:21]=1.P(=O)(O)(O)O.C(=O)([O-])[O-].[K+].[K+]>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:21]=[N:20][C:19]([N:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 11430Potassium CarbonateHCID 178452241HCID 178452241, compound

Product 1

HCID 178518349HCID 178518349, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A N,N-dimethylformamide mixture (0.35 mL) of tert-butyl 4-(5-{[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}pyridin-2-yl)piperazine-1-carboxylate (100 mg, 0.1738 mmol) and concentrated phosphoric acid (1.1 mL) is heated at 60 C for 2 h. The reaction solution is then treated with an ice-cold aqueous solution of potassium carbonate (1.8 g), and filtered, the solid which is washed exhaustively with water yielded 70 mg (85%) of the title compound as a solid. MS (ESI) m/z 476.1 (M+H)+1

Workup

  1. filtrationfiltered
  2. washthe solid which is washed exhaustively with water

Sources & evidence

ORD record
ord-fae3fed6c6434d318e4208d41931693e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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