1-Naphthalenesulfonyl chloride → HCID 9824069, compound

HRID 2119534Notes

Reaction equation

HRID 2119534 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[N:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1.[C:19]1([S:29](Cl)(=[O:31])=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[N:16][CH:17]=4)[N:12]([S:29]([C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21][CH:20]=4)(=[O:31])=[O:30])[CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 665601-Naphthalenesulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 9837669HCID 9837669, compound

Product 1

HCID 9824069HCID 9824069, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

from 3-(octahydro-7-indolizinyl)-1-H-5-azaindole (10 mg, 0.0415 mmol), 1-naphthalenesulfonyl chloride (15 mg, 0.072 mmol) and 1M NaN(TMS)2 (100 μL, 0.10 mmol) in THF (0.5 mL) at RT. The two enantiomers were separated by Chiral chromatography (Chiracel OD).

Workup

  1. customat RT
  2. customThe two enantiomers were separated by Chiral chromatography (Chiracel OD)

Sources & evidence

ORD record
ord-f97a081723554f9fae573a90d1fb3783
Source dataset
uspto-grants-2004_02
Patent number
US06686374B1

Reaction notes

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