1-Naphthalenesulfonyl chloride → HCID 9824069, compound

HRID 895418Notes

Reaction equation

HRID 895418 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-c598b5bfbac8465b8b731869a8b2b9f2
Source dataset
uspto-grants-2005_07
Patent number
US06916818B2

Reaction notes

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