3-Chloropropionyl chloride → 3-Chloro-N-[8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]propanamide

HRID 916353Notes

Reaction equation

HRID 916353 reaction equation
Cl.[NH2:2][CH:3]1[CH2:9][CH:8]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[CH:5]([CH2:6][CH2:7]2)[CH2:4]1.[Cl:23][CH2:24][CH2:25][C:26](Cl)=[O:27].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:23][CH2:24][CH2:25][C:26]([NH:2][CH:3]1[CH2:4][CH:5]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[CH:8]([CH2:7][CH2:6]2)[CH2:9]1)=[O:27]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 81531DiisopropylethylamineHCID 1317266004-(3-Amino-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile, hydrochloride

Product 1

HCID 692265953-Chloro-N-[8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was synthesized in the same way as 165RL23 using 165RL21 (320 mg, 1.15 mmol), 3-chloropropionyl chloride (120 μL, 1.27 mmol), DIPEA (220 μL, 1.27 mmol) and DMF (10 mL). The crude product was purified by column chromatography using ethyl acetate/MeOH (95:5) to give the title compound (318 mg, 75

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-208bb48df15845b295e5dad49d6238ac
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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