Difluoroacetic acid → HCID 86656367, compound

HRID 1942542Notes

Reaction equation

HRID 1942542 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([N:15]([CH:29]([CH3:31])[CH3:30])[C@@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)=[O:14])[CH:11]=2)[C:6]([CH3:33])([CH3:32])[C:5]1=[O:34].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[F:56][CH:57]([F:61])[C:58](O)=[O:59]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[F:56][CH:57]([F:61])[C:58]([NH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([N:15]([CH:29]([CH3:30])[CH3:31])[C@@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:17]3)=[O:14])[CH:11]=2)[C:6]([CH3:32])([CH3:33])[C:5]1=[O:34])=[O:59]

Participants

7

Reactant 4

HCID 9788Difluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67331329HCID 67331329, compound

Product 1

HCID 86656367HCID 86656367, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To tert-butyl (3R)-3-[{[1-(2-aminoethyl)-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl]-carbonyl}(isopropyl)amino]piperidine-1-carboxylate (300 mg) were added WSC (210 mg), HOBt (150 mg), triethylamine (0.30 ml), chloroform (5 ml), and difluoroacetic acid (79 mg), and the mixture was stirred at room temperature overnight. After the reaction was complete, the mixture was concentrated, and the obtained residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give the title compound (170 mg) as colorless amorphous.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-b80559811af6488ba547223bf817162b
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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