Water → HCID 12044956, compound

HRID 600663Notes

Reaction equation

HRID 600663 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[O:12]=[C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]1[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([CH:28]([O:32][C:33]2[CH:42]=[C:41]3[C:36]([CH:37]=[CH:38][N:39]=[C:40]3[N+:43]3C=CC=CC=3)=[CH:35][CH:34]=2)[CH2:29][CH2:30][CH3:31])=[O:27])=[CH:21][CH:20]=1.O>C(CN)O>[O:12]=[C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]1[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:27])[CH:28]([O:32][C:33]2[CH:42]=[C:41]3[C:36]([CH:37]=[CH:38][N:39]=[C:40]3[NH2:43])=[CH:35][CH:34]=2)[CH2:29][CH2:30][CH3:31])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 962WaterHCID 12044960HCID 12044960, compound

Product 1

HCID 12044956HCID 12044956, compound

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Procedure

The crude 1-(7-{1-[4-(2-oxopiperidin-1-yl)phenylcarbamoyl]butoxy}-isoquinolin-1-yl)pyridinium toluene4-sulfonate obtained in this way is dissolved in 4 ml of ethanolamine, and the mixture is stirred at room temperature for 42 hours. The reaction mixture is introduced into water and extracted with ethyl acetate. The organic phase is evaporated, and the residue is chromatographed on a silica-gel column, giving N-[4-(2-oxopiperidin-1-yl)phenyl]-2-(1-aminoisoquinolin-7-yloxy)pentanamide (“AA”) as a colourless solid; ESI 433.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is evaporated
  3. customthe residue is chromatographed on a silica-gel column

Sources & evidence

ORD record
ord-b6d0cd78c5c3456c8972ab16005ad5c1
Source dataset
uspto-grants-2011_03
Patent number
US07902223B2

Reaction notes

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