Hydrazine → HCID 59717979, compound

HRID 561340Notes

Reaction equation

HRID 561340 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[C:21]([CH2:26][N:27]4C(=O)C5C(=CC=CC=5)C4=O)[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5])[CH3:2].NN>CO>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[C:21]([CH2:26][NH2:27])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59717998HCID 59717998, compound

Product 1

HCID 59717979HCID 59717979, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of sulfonamide mixtures 54 (3.11 g, 5.97 mmol) in methanol (30 mL) was added hydrazine (3.4 mL). The resulting solution was stirred at 25° C. for 2 hr. The mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL). The aqueous layer was re-extracted with CH2Cl2. The organic extracts were combined, washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product. The crude material was purified by preparative TLC to provide 4-(5-aminomethyl-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester 55 as a white solid.

Workup

  1. customThe mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL)
  2. extractionThe aqueous layer was re-extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThe crude material was purified by preparative TLC

Sources & evidence

ORD record
ord-98bbcfc1c1ff4164be254d30f8e47cf8
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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