2-Naphthalenesulfonyl chloride → HCID 69918146, compound

HRID 2307828Notes

Reaction equation

HRID 2307828 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][N:10]([C:11]1[CH:12]=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=1)[S:29]([C:20]1[CH:21]=[CH:22][C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=1)(=[O:31])=[O:30])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 69918267Tert-butyl (2-[(5-bromopyridin-3-yl)amino]ethyl)carbamate

Product 1

HCID 69918146HCID 69918146, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Example 386A (50 mg, 0.158 mmol) in pyridine (2 mL) was added 2-naphthalenesulfonyl chloride (72 mg, 0.316 mmol) at rt. The formed yellow solution was stirred at rt for 15 h. Pyridine was removed by blowing with nitrogen and the residual yellow solid was purified by flash chromatography (30-60% EtOAc in hexane) to the desired product (81 mg, 100%). MS (DCI) m/z 506, 508 (M+1)+.

Workup

  1. customPyridine was removed
  2. customthe residual yellow solid was purified by flash chromatography (30-60% EtOAc in hexane) to the desired product (81 mg, 100%)

Sources & evidence

ORD record
ord-705a9d76c2814b86916438e5071a394a
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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