Selectfluor → HCID 58998495, compound

HRID 1593085Notes

Reaction equation

HRID 1593085 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][C:24]([F:32])=[C:25]([NH:30][CH3:31])[CH:26]=4)[C:21]3=[O:33])=[CH:16][CH:15]=2)=[O:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[B-](F)(F)(F)[F:35].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][C:24]([F:32])=[C:25]([NH:30][CH3:31])[C:26]=4[F:35])[C:21]3=[O:33])=[CH:18][CH:19]=2)=[O:12])(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 58998465HCID 58998465, compound

Product 1

HCID 58998495HCID 58998495, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(5-chlorothiophen-2-ylsulfonyl)-3-(4-(7-fluoro-6-(methylamino)-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)phenyl)urea (17 mg, 0.033 mmol) in DMF (2 mL) at room temperature, selectFluor (1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate), 32 mg, 0.090 mmol) was added. After being stirred at room temperature for 1 h, the reaction mixture was concentrated in vacuo. The residue was purified by RP-HPLC to give the titled compound as a powder (1 mg). ES-MS (M+H)+=527, 529 (Cl pattern).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-1139774f6f8949e7b75d9bf0ce265022
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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