Hydrazine hydrate (1:1) → HCID 71060257, compound

HRID 337234Notes

Reaction equation

HRID 337234 reaction equation
O.NN.[C:4]([O:8][C:9](=[O:38])[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1)([CH3:7])([CH3:6])[CH3:5]>C(O)C>[C:4]([O:8][C:9](=[O:38])[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][NH2:27])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1)([CH3:7])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 71059963HCID 71059963, compound

Product 1

HCID 71060257HCID 71060257, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydrazine monohydrate (0.11 ml, 2.4 mmol) was added to a stirred solution of {1-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzenesulfonyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (0.4 g, 0.8 mmol) in ethanol (10 ml), the mixture was heated to 70° C. and stirred at this temperature for 4 hours. After this time, the precipitate was removed by filtration and the filtrate was concentrated. The resulting residue was triturated with DCM and the resulting precipitate was collected by filtration and dried under vacuum to give the title compound (0.29 g, 98% yield) as a white solid. Tr=1.38 min, m/z (ES+) (M+Na)+ 392.

Workup

  1. customAfter this time, the precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was triturated with DCM
  4. filtrationthe resulting precipitate was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2335aad60be6461fa400b73fef17237e
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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