Dimethylformamide → 1-(4-Cyano-benzyl)-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid cyanomethyl-amide

HRID 512523Notes

Reaction equation

HRID 512523 reaction equation
[CH3:1][C:2]1[NH:7][CH:6]=[C:5]([C:8]([OH:10])=O)[C:4](=[O:11])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.BrC(C1C=C[C:36]([C:37]#[N:38])=CN=1)C.C[N:42]([CH:44]=O)C.C[N:47]1C(=O)CCC1>>[C:36]([CH2:37][NH:38][C:8]([C:5]1[C:4](=[O:11])[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[CH:13]=2)=[C:2]([CH3:1])[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:44]#[N:42])=[CH:25][CH:24]=2)[CH:6]=1)=[O:10])#[N:47]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 13387N-methyl-2-pyrrolidoneHCID 867115326-Methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acidHCID 867115466-(1-Bromoethyl)pyridine-3-carbonitrile

Product 1

HCID 867115741-(4-Cyano-benzyl)-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid cyanomethyl-amide

Procedure

Examples 47.1-47.20 are prepared in two steps: (1) Amide coupling as described for preparation 9.13 (Procedure A), substituting preparation 4 with preparation 5b and substituting aminoacetonitrile with the appropriate amines, respectively; (2) Alkylation as described for example 2.1, substituting benzyl bromide with preparation 15c, substituting preparation 5 with the intermediates from step 1, and substituting DMF with NMP.

Workup

  1. customExamples 47.1-47.20 are prepared in two steps
  2. custompreparation 4

Sources & evidence

ORD record
ord-5fcb79e9ceaa4191824118acd9503434
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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