4-Cyanobenzoic acid → HCID 71697354, compound

HRID 517590Notes

Reaction equation

HRID 517590 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:45][CH2:46][CH2:47][N:48]1[C:52](=[O:53])/[C:51](=[CH:54]/[C:55]2[CH:60]=[CH:59][C:58]([O:61][CH2:62][CH3:63])=[CH:57][CH:56]=2)/[S:50][C:49]1=[O:64]>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:45][CH2:46][CH2:47][N:48]2[C:52](=[O:53])/[C:51](=[CH:54]/[C:55]3[CH:60]=[CH:59][C:58]([O:61][CH2:62][CH3:63])=[CH:57][CH:56]=3)/[S:50][C:49]2=[O:64])=[O:9])=[CH:10][CH:11]=1)#[N:2]

Participants

7

Reactant 4

HCID 120874-Cyanobenzoic acidHCID 81531DiisopropylethylamineHCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71697354HCID 71697354, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-cyanobenzoic acid (46 mg, 0.31 mmol) in 3 mL of DMF was added DIPEA (131 μL, 0.75 mmol) followed by HBTU (114 mg, 0.30 mmol). After being stirred at room temperature for 1 h, compound 76 (101 mg, 0.25 mmol) was added and then the reaction mixture was stirred at room temperature overnight. The reaction solution was diluted with 50 mL of ethyl acetate and washed with water (30 mL×5), collected the organic layer, dried over Na2SO4, filtered, concentrated and purified by silica column chromatography (15% ethyl acetate in hexanes) to afford 97 mg (92.1%) of the title compound 25d as a light-yellow solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. washwashed with water (30 mL×5)
  3. customcollected the organic layer
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica column chromatography (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0c635c75a3f4491f93ce82daa957a13d
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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