Triethylamine → 6-{(SR)-1-[(3RS,4SR)-1-(4-Cyano-piperidine-1-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

HRID 1158667Notes

Reaction equation

HRID 1158667 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH:10]([CH:12]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:15][N:14]([C:25](Cl)=[O:26])[CH2:13]2)[CH3:11])=[N:7][CH:8]=1)#[N:2].CCN(CC)CC.[NH:35]1[CH2:40][CH2:39][CH:38]([C:41]#[N:42])[CH2:37][CH2:36]1>C(Cl)Cl>[C:41]([CH:38]1[CH2:39][CH2:40][N:35]([C:25]([N:14]2[CH2:15][CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH:12]([CH:10]([O:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH3:11])[CH2:13]2)=[O:26])[CH2:36][CH2:37]1)#[N:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1382234-CyanopiperidineHCID 86628181(3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride

Product 1

HCID 673276916-{(SR)-1-[(3RS,4SR)-1-(4-Cyano-piperidine-1-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride (30 mg, 0.070 mmol) in CH2Cl2 (4 mL) were added Et3N (0.015 mL, 0.11 mmol) and piperidine-4-carbonitrile (commercially available) (9 mg, 0.084 mmol). Stirring was continued overnight, and the reaction mixture was concentrated under vacuo and directly purified by flash chromatography (SiO2, EtOAc) to yield 24 mg (69%) the title compound as light yellow oil. ES-MS m/e: 498.0 (M+H+).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuo
  2. customdirectly purified by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-105de65fd74d44909e7ed76bd1bb57de
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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