Sodium Carbonate → (R)-methyl 4-(1-(1-(4-cyanobenzyl)piperidine-2-carboxamido)cyclopropyl)benzoate

HRID 712863Notes

Reaction equation

HRID 712863 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)#[N:24].C([O-])([O-])=O.[Na+].[Na+]>>[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]2[C:7]([NH:9][C:10]2([C:13]3[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=3)[CH2:12][CH2:11]2)=[O:8])=[CH:27][CH:26]=1)#[N:24]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 71204684HCID 71204684, compound

Product 1

HCID 71204686(R)-methyl 4-(1-(1-(4-cyanobenzyl)piperidine-2-carboxamido)cyclopropyl)benzoateYield 74.6%

Procedure

The title compound (D121) (35 mg) was prepared according to the general procedure for substituted benzyl amines preparation starting from (R)-methyl 4-(1-(piperidine-2-carboxamido)cyclopropyl)benzoate (D87) (34 mg) and 4-Cyanobenzylbromide (33 mg). (Na2CO3: 4 eq; reaction time: 18 hrs; 68° C.)

Sources & evidence

ORD record
ord-1c3978dfcf4e487baf2725a52e61e444
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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