Hydrazine hydrate (1:1) → N-[3-[[4-(Aminomethyl)benzoyl]amino][1,1'-biphenyl]-4-yl]carbamic Acid tert-Butyl Ester

HRID 1013531Notes

Reaction equation

HRID 1013531 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([NH:21][C:22]2[CH:23]=[C:24]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:25]=[CH:26][C:27]=2[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:20])=[CH:15][CH:14]=1.O.NN>CCO>[NH2:3][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([NH:21][C:22]2[CH:23]=[C:24]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:25]=[CH:26][C:27]=2[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57925844HCID 57925844, compound

Product 1

HCID 57925864N-[3-[[4-(Aminomethyl)benzoyl]amino][1,1'-biphenyl]-4-yl]carbamic Acid tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,1-dimethylethyl {3-[({4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}carbonyl)amino]biphenyl-4-yl}carbamate (17 g, 31 mmol) and hydrazine hydrate (3.01 mL, 62.1 mmol) were stirred in refluxing EtOH (135 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 (10% [MeOH+1% NH4OH]-DCM) to give 1,1-dimethylethyl [3-({[4-(aminomethyl)phenyl]carbonyl}amino)biphenyl-4-yl]carbamate as a white solid. 1H NMR (d6-DMSO, 600 MHz) δ 9.86 (s, 1H), 8.77 (s, 1H), 7.90 (d, J=7.8 Hz, 2H), 7.85 (d, J=1.8 Hz, 1H), 7.62 (m, 3H), 7.49 (m, 3H), 7.44 (t, J=7.5 Hz, 2H), 7.33 (t, J=7.5 Hz, 1H), 3.79 (s, 2H), 1.45 (s, 9H).

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 (10% [MeOH+1% NH4OH]-DCM)

Sources & evidence

ORD record
ord-a17eb2f27ef74f0695bebf544ecbc69b
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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