Hydrochloric Acid → HCID 24969294, compound

HRID 2235000Notes

Reaction equation

HRID 2235000 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]C)=[N:20][CH:21]=2)[CH2:3]1.Cl>O1CCOCC1.O>[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:27])=[O:26])[C:19](=[O:22])[NH:20][CH:21]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58988124HCID 58988124, compound

Product 1

HCID 24969294HCID 24969294, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
70 °C

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 dioxan (2 ml) was treated with 4.0M hydrogen chloride in dioxan (1 ml) and water (0.5 ml). The mixture was heated at 70° C. for 4 hours. The solvent was evaporated and the residue dissolved in ethanol (5 ml) and 2M hydrochloric acid (2 ml). 10% Palladium on carbon (10 mg) was added and the mixture stirred in a hydrogen atmosphere for 4 hours. The mixture was filtered through ‘celite’ and the solvent was evaporated. Purification by MDAP gave the title compound (E15). MS (ES+) m/e 461 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethanol (5 ml)
  3. addition10% Palladium on carbon (10 mg) was added
  4. filtrationThe mixture was filtered through ‘celite’ and the solvent
  5. customwas evaporated
  6. customPurification by MDAP

Sources & evidence

ORD record
ord-da12a3fccf7d4420a2fc604017b11297
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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