2-Naphthalenesulfonyl chloride → HCID 69919218, compound

HRID 2307819Notes

Reaction equation

HRID 2307819 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[N:22][CH:21]=[CH:20]3)[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[S:38](Cl)(=[O:40])=[O:39]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][N:10]([C:11]1[CH:12]=[N:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[N:22][CH:21]=[CH:20]3)[CH:16]=1)[S:38]([C:29]1[CH:30]=[CH:31][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=1)(=[O:40])=[O:39])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 69918479HCID 69918479, compound

Product 1

HCID 69919218HCID 69919218, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Example 386B (70 mg, 0.192 mmol) in pyridine (3 mL) was added 2-naphthalenesulfonyl chloride (87 mg, 0.384 mmol) at rt. The formed yellow solution was stirred at rt for 15 h. Pyridine was removed under reduced pressure and the residual oil was purified by flash chromatography (0-15% CH3OH in 2:1 EtOAc/hexane) to provide the desire product (69 mg, 65%). MS (APCI) m/z 555 (M+1)+.

Workup

  1. customPyridine was removed under reduced pressure
  2. customthe residual oil was purified by flash chromatography (0-15% CH3OH in 2:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-9663016458654aea89adebbba26e3f35
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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