Hydrazine → Tert-butyl [2-{[4-(aminomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate

HRID 1013524Notes

Reaction equation

HRID 1013524 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[CH:40]=[CH:39][C:16]([C:17]([NH:19][C:20]2[CH:25]=[C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)[CH:23]=[CH:22][C:21]=2[NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:18])=[CH:15][CH:14]=1.NN>CCO>[NH2:3][CH2:12][C:13]1[CH:40]=[CH:39][C:16]([C:17]([NH:19][C:20]2[CH:25]=[C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)[CH:23]=[CH:22][C:21]=2[NH:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58283975Tert-butyl [2-({4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzoyl}amino)-4-(2-thienyl)phenyl]carbamate

Product 1

HCID 57925930Tert-butyl [2-{[4-(aminomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tert-butyl [2-({4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzoyl}amino)-4-(2-thienyl)phenyl]carbamate (4.4 g, 7.95 mmol) and hydrazine (0.495 mL, 15.90 mmol) were stirred in refluxing EtOH (35 mL) for 5 hours. Room temperature was attained and the white precipitate removed by filtration and washed with EtOH. The filtrate was concentrated in vacuo and purified by MPLC (1-12.5% [MeOH+1% NH4OH]-DCM) to give tert-butyl [2-{[4-(aminomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate as a white solid.

Workup

  1. customRoom temperature
  2. customthe white precipitate removed by filtration
  3. washwashed with EtOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by MPLC (1-12.5% [MeOH+1% NH4OH]-DCM)

Sources & evidence

ORD record
ord-c8051082d4a94d31ac180b5c63108cb3
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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