2-Bromobenzonitrile → 4-(2-Cyanophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic Acid [4-(3-dimethylamino-pyrrolidin-1-yl)phenyl]amide

HRID 1354740Notes

Reaction equation

[CH3:1][N:2]([CH3:32])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([N:17]3[CH2:22][CH:21]=[C:20](B4OC(C)(C)C(C)(C)O4)[CH2:19][CH2:18]3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1.Br[C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[C:36]#[N:37]>>[CH3:1][N:2]([CH3:32])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([N:17]3[CH2:22][CH:21]=[C:20]([C:34]4[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=4[C:36]#[N:37])[CH2:19][CH2:18]3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1

Participants

Reactant 2

HCID 162722-Bromobenzonitrile

HCID 671479464-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Product 1

HCID 588668514-(2-Cyanophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic Acid [4-(3-dimethylamino-pyrrolidin-1-yl)phenyl]amide

Procedure

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide was reacted with 2-bromobenzonitrile by method O-a. This resulted in the product with the molecular weight of 415.54 (C25H29N5O); MS (ESI): 416 (M+H+)

Workup

customThis resulted in the product with the molecular weight of 415.54 (C25H29N5O)

Sources & evidence

ORD record: ord-5b55927a25e5493c89053b6da4531687
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223788B2

Reaction notes

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