Piperidine → HCID 118340294, compound

HRID 1477153Notes

Reaction equation

HRID 1477153 reaction equation
N1CCCCC1.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[NH:15][C:16]([CH:18]1[C:26]([CH3:28])([CH3:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]1[C:29](=[O:52])[C@@H:30]([NH:34]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)[CH:31]([CH3:33])[CH3:32])=[O:17]>C(Cl)Cl>[NH2:34][CH:30]([CH:31]([CH3:33])[CH3:32])[C:29]([N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]([CH3:28])([CH3:27])[C@H:18]1[C:16]([NH:15][C:9]1[C:10]([F:14])=[CH:11][CH:12]=[CH:13][C:8]=1[F:7])=[O:17])=[O:52]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 118340312HCID 118340312, compound

Product 1

HCID 118340294HCID 118340294, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperidine (0.1 mL, 1.01 mmol, Eq: 9.86) was added to a solution of (S)-(9H-fluoren-9-yl)methyl 1-(2-(2,6-difluorophenylcarbamoyl)-3,3-dimethylindolin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (71 mg, 102 μmol, Eq: 1.00) in DCM (2 mL) and the resulting solution was stirred at rt for 3 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 4 g, 0% to 10% MeOH in DCM) to give (S)-1-(2-amino-3-methylbutanoyl)-N-(2,6-difluorophenyl)-3,3-dimethylindoline-2-carboxamide (32 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (silica gel, 4 g, 0% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-b2b404debe794a198a1786b6c9247650
Source dataset
uspto-grants-2016_08
Patent number
US09403768B2

Reaction notes

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