1-(4-Azidoquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one → 1-(4-Aminoquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one

HRID 1432990Notes

Reaction equation

HRID 1432990 reaction equation
[N:1]([C:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][N:15]3[CH2:20][CH2:19][N:18]([S:21]([C:24]4[S:28][C:27]5[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:26]=5[CH:25]=4)(=[O:23])=[O:22])[CH2:17][C:16]3=[O:34])=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1)=[N+]=[N-]>C(O)(=O)C.CO.[Pd]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][N:15]3[CH2:20][CH2:19][N:18]([S:21]([C:24]4[S:28][C:27]5[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:26]=5[CH:25]=4)(=[O:22])=[O:23])[CH2:17][C:16]3=[O:34])=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 179852221-(4-Azidoquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one

Product 1

HCID 179852331-(4-Aminoquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-oneYield 82.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

A suspension of 1-(4-azidoquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one (0.50 g, 1.04 mmol) in 100 mL of acetic acid/methanol (˜1:10) is treated with 10% Pd/C (0.15 g) and stirred under hydrogen for 1.5 hours. The resulting solution is filtered through Celite and the filtrate is evaporated in vacuo. The organic layer is concentrated and the residue is purified by reverse phase HPLC (gradient elution of 30% of 0.1% aqueous TFA/acetonitrile to 100% acetonitrile) and lyopholized to give the title compound (0.39 g, 0.86 mmol). MS (ISP) m/z 487, 489, (M+H), Cl pattern.

Workup

  1. filtrationThe resulting solution is filtered through Celite
  2. customthe filtrate is evaporated in vacuo
  3. concentrationThe organic layer is concentrated
  4. customthe residue is purified by reverse phase HPLC (gradient elution of 30% of 0.1% aqueous TFA/acetonitrile to 100% acetonitrile)

Sources & evidence

ORD record
ord-f75b25d8a78746f489de43548c5432a0
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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