Hydrazine → 3-{1-[(2-aminoethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

HRID 2267509Notes

Reaction equation

HRID 2267509 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][S:14]([N:17]1[CH2:22][CH2:21][CH:20]([C:23]2[C:31]3[C:26](=[C:27]([C:38]([NH2:40])=[O:39])[CH:28]=[C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:30]=3)[NH:25][CH:24]=2)[CH2:19][CH2:18]1)(=[O:16])=[O:15].NN>CCO>[NH2:3][CH2:12][CH2:13][S:14]([N:17]1[CH2:18][CH2:19][CH:20]([C:23]2[C:31]3[C:26](=[C:27]([C:38]([NH2:40])=[O:39])[CH:28]=[C:29]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:30]=3)[NH:25][CH:24]=2)[CH2:21][CH2:22]1)(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 590033673-(1-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide

Product 1

HCID 116116193-{1-[(2-aminoethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(1-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide (70 mg, 0.13 mmol) in EtOH (2 mL) at room temperature, hydrazine (0.3 mL) was added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the resulting residue purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give the title compound (26.9 mg, 50%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting residue purified by reverse phase HPLC
  3. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-8bd1cbea024342989b6a0b7efd977113
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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