Acetic Acid → HCID 56658872, compound

HRID 2061598Notes

Reaction equation

HRID 2061598 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]3[CH2:17][CH:18]([C:20]4[O:24][N:23]=[C:22]([CH3:25])[N:21]=4)[CH2:19][CH:12]2[C:13](=[CH:27]O)[C:14](=O)[CH2:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)(=O)C.O.[NH2:34][NH2:35]>CCO.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:16]3[CH2:15][C:14]4[NH:34][N:35]=[CH:27][C:13]=4[CH:12]2[CH2:19][CH:18]([C:20]2[O:24][N:23]=[C:22]([CH3:25])[N:21]=2)[CH2:17]3)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 67308098HCID 67308098, compound

Product 1

HCID 56658872HCID 56658872, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 9-[(4-chlorophenyl)sulfonyl]-2-(hydroxymethylidene)-7-(3-methyl-1,2,4-oxadiazol-5-yl)-9-azabicyclo[3.3.1]nonan-3-one (53) (0.38 g, 0.902 mmol) in EtOH (5 mL) was added glacial acetic acid (0.1 mL) followed by hydrazine monohydrate (0.44 mL, 9.02 mmol). The reaction mixture was stirred at room temperature for 2 h and then at 50° C. for a further 2 h. The resulting solution was diluted with EtOAc and washed with H2O. The organic phase was dried (Na2SO4), filtered, concentrated and purified by silica gel column chromatography (eluant hexane/EtOAc, 9/1 to 2/8) and preparative HPLC to give 10-[(4-chlorophenyl)sulfonyl]-6-(3-methyl-1,2,4-oxadiazol-5-yl)-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole (54). MS (ESI) 420.1 (M+H). 1H NMR (300 MHz, CDCl3) δ 7.67 (d, J=8.8 Hz, 2H), 7.52 (s, 1H), 7.39 (d, J=8.8 Hz, 2H), 5.43 (bs, 1H), 4.66 (bs, 1H), 3.06 (m, 1H), 2.72 (d, J=17.6 Hz, 1H), 2.34 (s, 3H), 2.32-2.09 (m, 4H).

Workup

  1. waitat 50° C. for a further 2 h
  2. washwashed with H2O
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (eluant hexane/EtOAc, 9/1 to 2/8) and preparative HPLC

Sources & evidence

ORD record
ord-5471e61eb4264de1ba7b23667ce678b8
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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