Sodium Carbonate → HCID 22503117, compound

HRID 1814543Notes

Reaction equation

HRID 1814543 reaction equation
C(N(S(F)(F)[F:7])CC)C.[ClH:10].Cl.[CH2:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[C:22]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH2:39][CH2:40][CH2:41]O)(=[O:38])=[O:37])=[CH:32][CH:31]=3)[N:21]=2)[CH2:16][CH2:15]1)[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[ClH:10].[ClH:10].[CH2:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[C:22]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH2:39][CH2:40][CH2:41][F:7])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[N:21]=2)[CH2:16][CH2:15]1)[CH3:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluoride2×HCID 22502496HCID 22502496, compound

Product 1

HCID 22503117HCID 22503117, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Diethylaminosulfur trifluoride (DAST, 0.14 ml) was added to anhydrous methylene chloride (3 ml), and the resulting mixture was stirred at −78° C. in nitrogen atmosphere, to which was then added a solution of 1-(4-ethylpiperazin-1-yl)-3-[4-(3-hydroxypropyl)sulfonylphenyl]isoquinoline (0.31 g) obtained in Example 352 in methylene chloride (5 ml), and the mixture was further stirred for 6 hr. DAST (0.09 ml) was further added thereto, and the resulting mixture was further stirred overnight. The bulk temperature was raised to room temperature. The reaction solution was diluted with chloroform, followed by the addition of a 10% aqueous solution of sodium carbonate. The organic layer was separated, and then it was washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 0.23 g of the free compound of the title compound as a pale brown viscous oil.

Workup

  1. stirringthe mixture was further stirred for 6 hr
  2. stirringthe resulting mixture was further stirred overnight
  3. temperatureThe bulk temperature was raised to room temperature
  4. customThe organic layer was separated
  5. washit was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-9078eedc1d2d479fbc11ef7b0df6715d
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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