Triphenylphosphine → HCID 22712398, compound

HRID 1883111Notes

Reaction equation

HRID 1883111 reaction equation
[C:1]([CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[NH:13][C:14]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[C:20]([OH:25])[CH:19]=2)=[O:15])=[O:6])#[N:2].[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34]O)[CH2:29][CH2:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[C:1]([CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[NH:13][C:14]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[C:20]([O:25][CH2:34][CH2:33][N:30]1[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]1)[CH:19]=2)=[O:15])=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 5462977Diethyl azodicarboxylateHCID 20732623HCID 20732623, compound

Product 1

HCID 22712398HCID 22712398, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 85 mg (0.25 mM) 6-Hydroxy-1H-indole-2-carboxylic acid [2-(cyanomethyl-carbamoyl)-cyclohexyl]-amide in 5 ml dichloromethane at 0° C. was added 144 mg (1 mM) 2-(4-Methyl-piperazin-1-yl)ethanol, 262 mg (1 mM) triphenylphosphine and 131 mg (0.75 mM) DEAD. After several hours the mixture was allowed to warm to room temperature and stir overnight. The reaction mixture was purified directly on a preparative TLC plate and eluted with 10% methanol/dichloromethane. The product was then partitioned between 1 M HCl and ethyl acetate, the aqueous layer was neutralized and extracted with ethyl acetate, dried over magnesium sulfate and stripped to give 18.9 mg 6-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-1H-indole-2-carboxylic acid [2-(cyanomethyl-carbamoyl)-cyclohexyl]-amide.

Workup

  1. waitAfter several hours the mixture was allowed
  2. customThe reaction mixture was purified directly on a preparative TLC plate
  3. washeluted with 10% methanol/dichloromethane
  4. customThe product was then partitioned between 1 M HCl and ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-c9650e7fbb8242e1a27d2d3777e3de63
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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