Hydrazine hydrate (1:1) → HCID 68311076, compound

HRID 470698Notes

Reaction equation

HRID 470698 reaction equation
O.NN.O[N:5]1C2C=CC=CC=2N=[N:6]1.Cl.C(N=C=NCCCN(C)C)C.[CH2:26]([O:33][C:34]([NH:36][C@H:37]1[CH2:45][O:44][C@H:40]([C:41](O)=[O:42])[CH2:39][CH2:38]1)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[NH:5]([C:41]([C@H:40]1[O:44][CH2:45][C@H:37]([NH:36][C:34](=[O:35])[O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:38][CH2:39]1)=[O:42])[NH2:6]

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68310074HCID 68310074, compound

Product 1

HCID 68311076HCID 68311076, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydrazine monohydrate (0.23 ml, 3.86 mmol), 1-hydroxybenzotriazole (434 mg, 3.21 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (740 mg, 3.86 mmol) were added to an N,N-dimethylformamide (16 ml) solution of the compound (898 mg, 3.21 mmol) obtained in Step 3 above at room temperature and the resulting mixture was stirred for 18 hours. The reaction mixture was subjected to extraction with chloroform:methanol [10:1 (v/v)] and the organic layer was washed with saturated sodium bicarbonate solution and then dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography [dichloromethane:methanol=49:1→13:1 (v/v)] to give 811 mg (86%) of the title compound as a colorless solid.

Workup

  1. extractionThe reaction mixture was subjected to extraction with chloroform
  2. washmethanol [10:1 (v/v)] and the organic layer was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography [dichloromethane:methanol=49:1→13:1 (v/v)]

Sources & evidence

ORD record
ord-29206c916bcd45999fc1a8a5378ceaf7
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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