Hydrazine → HCID 11453978, compound

HRID 602812Notes

Reaction equation

HRID 602812 reaction equation
[C:1]1([S:7]([C:10]([CH:29]2[CH2:41][C:32]3[NH:33][C:34]4[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][C:39]=4[C:31]=3[CH2:30]2)([F:28])[C:11]2[O:15][N:14]=[C:13]([CH2:16][N:17]3C(=O)C4C(=CC=CC=4)C3=O)[N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN>CCO>[C:1]1([S:7]([C:10]([CH:29]2[CH2:41][C:32]3[NH:33][C:34]4[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][C:39]=4[C:31]=3[CH2:30]2)([F:28])[C:11]2[O:15][N:14]=[C:13]([CH2:16][NH2:17])[N:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 11444703HCID 11444703, compound

Product 1

HCID 11453978HCID 11453978, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 420 mg (0.7 mmol) of (RS,SR)-2-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-isoindole-1,3-dione in 50 mL EtOH at RT, was added 0.1 mL (2.1 mmol, 3 eq) hydrazine. The reaction mixture was heated at 80° C. over 3 hours 30 minutes. After cooling down, the reaction was quenched with a 1M solution of HCl, and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (CH2Cl2/MeOH 95/5) yielded 210 mg (64%) of (RS,SR)-C-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-yl}-methylamine as a light brown powder, MS: 461 (MH+).

Workup

  1. temperatureAfter cooling down
  2. customthe reaction was quenched with a 1M solution of HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-87d986684bbd468da45eff18d37c1c1b
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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