3-Cyanobenzoic acid → HCID 57471631, compound

HRID 42232Notes

Reaction equation

HRID 42232 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)#[N:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:55]1[CH2:60][CH2:59][CH:58]([C:61]2[C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[NH:63][CH:62]=2)[CH2:57][CH2:56]1>CN(C=O)C>[NH:63]1[C:64]2[C:69](=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:61]([CH:58]2[CH2:59][CH2:60][N:55]([C:6]([C:5]3[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=3)[C:1]#[N:2])=[O:8])[CH2:56][CH2:57]2)=[CH:62]1

Participants

7

Reactant 5

HCID 158753-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57471631HCID 57471631, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Cyano-benzoic acid (0.09 g, 0.6 mmol) is dissolved in 3 ml of DMF, then HBTU (0.28 g, 0.75 mmol), HOBt (0.10 g, 0.75 mmol) and DIPEA (0.26 g, 2.0 mmol) are added. The mixture is stirred at RT for 20 min before adding the 3-piperidin-4-yl-1H-indole (0.09 g, 0.6 mmol). The reaction was stirred at RT for 3 hours, monitored with LC/MS. The organic solvent is removed under the reduced pressure and the residue is purified by a silica gel flash column using heptane and ethyl acetate as the elutes.

Workup

  1. stirringThe reaction was stirred at RT for 3 hours
  2. customThe organic solvent is removed under the reduced pressure
  3. customthe residue is purified by a silica gel flash column

Sources & evidence

ORD record
ord-f4554b544fa147819ef2c8d91cf0d31e
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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