2-Chlorobenzenesulfonyl chloride → HCID 68552215, compound

HRID 1868088Notes

Reaction equation

HRID 1868088 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[C:4]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([N:12]1[CH2:11][CH2:10][CH:9]([C:4]2[C:3]([C:2]([F:15])([F:1])[F:16])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 28952599HCID 28952599, compound

Product 1

HCID 68552215HCID 68552215, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the amine from Step 13BE (100 mg, 0.43 mmol) in CH2Cl2 (2.9 mL) was added 2-chlorobenzenesulfonyl chloride (113 mg, 73 μl, 0.52 mmol) and sat. NaHCO3 (1.4 mL). The biphasic mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (3 mL) and poured into a Phase Separator cartridge. The organic phase was concentrated and purified by flash chromatography (elution with 0-20% EtOAc-hex). Lyophilization then afforded the title compound (121 mg), a white solid, in 70% yield. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.79 (d, J=13.6 Hz, 2H), 2.09-2.23 (m, 2H), 2.82-2.92 (m, 2H), 3.08 (t, J=11.9 Hz, 1H), 4.02 (d, J=12.4 Hz, 2H), 7.21-7.27 (m, 1H), 7.37-7.44 (m, 1H), 7.46-7.52 (m, 1H), 7.53-7.59 (m, 1H), 7.89 (dd, J=8.0, 1.6 Hz, 1H), 8.09 (d, J=6.3 Hz, 1 H), 8.73 (d, J=3.5 Hz, 1H). HRMS: calcd for C17H16ClF3N2O2S+H+, 405.06458. found (ESI-FTMS, [M+H]1+), 405.0652.

Workup

  1. additionpoured into a Phase Separator cartridge
  2. concentrationThe organic phase was concentrated
  3. custompurified by flash chromatography (elution with 0-20% EtOAc-hex)

Sources & evidence

ORD record
ord-a556f7d4643445ff8da4d6166df2105e
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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