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

HRID 559310Notes

Reaction equation

HRID 559310 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH2:11][CH:10]2[CH:22]([O:24][C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=2)[CH3:23])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].I[CH2:36][C:37]#[N:38]>C1COCC1>[C:37]([CH2:36][N:19]1[CH2:20][CH2:21][CH:16]([C:14]([N:12]2[CH2:13][CH:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH:10]([CH:22]([O:24][C:25]3[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=3)[CH3:23])[CH2:11]2)=[O:15])[CH2:17][CH2:18]1)#[N:38]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69356IodoacetonitrileHCID 669991306-{(SR)-1-[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

Product 1

HCID 767007356-{(SR)-1-[(3RS,4SR)-1-(1-Cyanomethyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-{(SR)-1-[(3RS,4SR)-4-(3,4-dichloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile (VIII-B-1) (25 mg, 0.053 mmol) in THF (2 mL) was added NaH (2.4 mg, 55% purity, 0.056 mmol). After 10 min. 2-iodo acetonitrile (13 mg, 0.079 mmol) was added and stirring was continued at RT overnight.

Workup

  1. waitwas continued at RT overnight

Sources & evidence

ORD record
ord-d4e03c266a9f42b89c2e1ff79d377b47
Source dataset
uspto-grants-2011_11
Patent number
US08063075B2

Reaction notes

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