Hydrochloric Acid → HCID 59007046, compound

HRID 130476Notes

Reaction equation

HRID 130476 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:12]=[CH:13][C:14]=2[O:15][CH2:16][CH3:17])[CH2:3]1.[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C.C1(C)C=CC=CC=1>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:30]4[S:29][CH:33]=[CH:32][CH:31]=4)=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:12]=[CH:13][C:14]=2[O:15][CH2:16][CH3:17])[CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 69197732HCID 69197732, compound

Product 1

HCID 59007046HCID 59007046, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of N-[3-(cis-3,5-dimethyl-1-piperazinyl)-4-(ethyloxy)phenyl]-4-iodobenzenesulfonamide (E94) (206 mg, 0.4 mmol), 2-thienylboronic acid (103 mg, 0.8 mmol), 2M aqueous sodium carbonate solution (1 ml, 2 mmol) and bis(triphenylphosphine)palladium(II) chloride (14 mg, 0.02 mmol) in 1:1 toluene:ethanol (3 ml) was stirred in a microwave reactor (set at high absorbance) at 125° C. for 15 minutes. After cooling to room temperature the reaction mixture was acidified with 5N hydrochloric acid the mixture applied to an SCX ion exchange cartridge (Varian bond-elute) and washed with methanol and 2M ammonia in methanol. The combined basic fractions were concentrated in vacuo and the residue purified by chromatography on silica gel to afford the desired product (E310). MS (ES+) m/e 472 [M+H]+.

Workup

  1. washapplied to an SCX ion exchange cartridge (Varian bond-elute)
  2. washwashed with methanol and 2M ammonia in methanol
  3. concentrationThe combined basic fractions were concentrated in vacuo
  4. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-51d2faa8de644c22ab3d0aa31eff3ea8
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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