Sodium Hydroxide → HCID 45279329, compound

HRID 2061606Notes

Reaction equation

HRID 2061606 reaction equation
[OH-].[Na+].ClC1C=CC(S([N:13]2[C:17]3[CH2:18][CH:19]4[N:24]([S:25]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)(=[O:27])=[O:26])[CH:23]([C:16]=3[CH:15]=[N:14]2)[CH2:22][CH:21]([C:35]#[N:36])[CH2:20]4)(=O)=O)=CC=1.ClC1C=CC(S(N2C=C3C4N(S(C5C=CC(Cl)=CC=5)(=O)=O)C(CC3=N2)CC(C#N)C4)(=O)=O)=CC=1>C1COCC1.CCOC(C)=O>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([S:25]([N:24]2[CH:19]3[CH2:18][C:17]4[NH:13][N:14]=[CH:15][C:16]=4[CH:23]2[CH2:22][CH:21]([C:35]#[N:36])[CH2:20]3)(=[O:27])=[O:26])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67303576HCID 67303576, compoundHCID 67308401HCID 67308401, compound

Product 1

HCID 45279329HCID 45279329, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydroxide (130 μL of a 3N aqueous solution) was added to a solution of 1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole-6-carbonitrile and 2,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-2H-4,8-epiminocycloocta[c]pyrazole-6-carbonitrile (61) (69 mg, 0.13 mmol) in THF (0.5 mL) and the resulting solution was stirred at room temperature for 5 h. The reaction mixture was diluted with EtOAc and washed with brine. The organic phase was dried (Na2SO4), filtered, concentrated and purified by preparative HPLC to give 10-[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole-6-carbonitrile (62). MS (ESI) 363.1 (M+H). 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J=8.8 Hz, 2H), 7.43 (s, 1H), 7.35 (d, J=8.8 Hz, 2H), 5.38 (bs, 1H), 4.61-4.52 (m, 1H), 2.93 (dd, J=17.0, 6.6 Hz, 1H), 2.71-2.52 (m, 2H), 2.32-1.98 (m, 4H).

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-c4ba4e87b8df4f70b2421ae6fc766af0
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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