Thionyl Chloride → 5-(2-Azepan-1-ylethyl)pyridine-2-carbonyl chloride hydrochloride

HRID 1434000Notes

Reaction equation

HRID 1434000 reaction equation
BrC1N=CC(CCN2CCCCCC2)=CC=1.[N:17]1([CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([O-:34])=O)=[N:30][CH:31]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Li+].S(Cl)([Cl:38])=O>>[ClH:38].[N:17]1([CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([Cl:38])=[O:34])=[N:30][CH:31]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 579343051-(2-(6-Bromopyridin-3-yl)ethyl)azepaneHCID 66628050Lithium 5-(2-azepan-1-ylethyl)pyridine-2-carboxylate

Product 1

HCID 866052435-(2-Azepan-1-ylethyl)pyridine-2-carbonyl chloride hydrochloride

Conditions

Temperature
90 °C

Procedure

Synthesized from 1-[2-(6-bromopyridin-3-yl)ethyl]azepane (400 mg) according to an analogous synthetic method to Preparation Example 51, to the total amount of lithium 5-(2-azepan-1-ylethyl)pyridine-2-carboxylate crude product was added thionyl chloride (8 ml), the solution was stirred for 30 minutes at 90° C., then the reaction solution was concentrated in vacuo to provide 5-(2-azepan-1-ylethyl)pyridine-2-carbonyl chloride hydrochloride (640 mg). Synthesized from this compound (320 mg) and pivalic acid 6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (40 mg) according to an analogous synthetic method to Example 152, the title compound (7 mg) was obtained.

Workup

  1. concentrationthe reaction solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2cbd9806dcee41d8a55079eaa418f959
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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