Hydrochloric Acid → HCID 68680072, compound

HRID 2234999Notes

Reaction equation

HRID 2234999 reaction equation
[CH3:1][C@H:2]1[N:7](CC2C=CC=CC=2)[C@@H:6]([CH3:15])[CH2:5][N:4]([C:16]2[CH:17]=[C:18]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[O:35][C:36]([CH3:39])=[CH:37][CH:38]=4)=[C:30]([F:40])[CH:29]=3)(=[O:27])=[O:26])[C:19]([O:22][CH3:23])=[N:20][CH:21]=2)[CH2:3]1.[H][H].[ClH:43]>C(O)C.[Pd]>[ClH:43].[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:15])[CH2:5][N:4]([C:16]2[CH:17]=[C:18]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[O:35][C:36]([CH3:39])=[CH:37][CH:38]=4)=[C:30]([F:40])[CH:29]=3)(=[O:26])=[O:27])[C:19]([O:22][CH3:23])=[N:20][CH:21]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58988124HCID 58988124, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68680072HCID 68680072, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[5-[cis-3,5-dimethyl-4-(phenylmethyl)-1-piperazinyl]-2-(methyloxy)-3-pyridinyl]-3-fluoro-4-(5-methyl-2-furanyl)benzenesulfonamide (D31) (60 mg, 0.1 mmol) in ethanol (5 ml) and 2M hydrochloric acid (0.5 ml) containing 10% palladium on carbon (10 mg) was stirred in a hydrogen atmosphere for 2 hours. The mixture was filtered through ‘celite’ and the solvent evaporated. Purification of the residue by flash chromatography eluting with 5% methanol in dichloromethane followed by treatment with 1.0M hydrogen chloride in diethyl ether gave the title compound (E13). MS (ES+) m/e 475 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through ‘celite’ and the solvent
  2. customevaporated
  3. customPurification of the residue by flash chromatography
  4. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-f489bf15b04d4771bfb318721bbedd62
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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