Ammonium Hydroxide → HCID 11340480, compound

HRID 602780Notes

Reaction equation

HRID 602780 reaction equation
C[O:2][C:3]([C:5]1[N:9]=[C:8]([C:10]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])([CH:12]2[CH2:24][C:15]3[NH:16][C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][C:22]=4[C:14]=3[CH2:13]2)[F:11])[O:7][N:6]=1)=O.[OH-].[NH4+:35]>CCO>[C:28]1([S:25]([C:10]([CH:12]2[CH2:24][C:15]3[NH:16][C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][C:22]=4[C:14]=3[CH2:13]2)([F:11])[C:8]2[O:7][N:6]=[C:5]([C:3]([NH2:35])=[O:2])[N:9]=2)(=[O:27])=[O:26])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 11317811HCID 11317811, compound

Product 1

HCID 11340480HCID 11340480, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 70 mg (0.14 mmol) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid methyl ester in 3 mL of EtOH, were added 0.5 mL of an ammonium hydroxide solution (25% in water) and stirred over night. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried over Na2SO4, filtered and evaporated. Recrystallisation in Et2O afforded 60 mg (86%) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid amide as a light orange crystals, MS: 475 (MH+).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customRecrystallisation in Et2O

Sources & evidence

ORD record
ord-cc84dd5725e44347adf2f86c5187de35
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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