Triethylamine → HCID 70980561, compound

HRID 1475511Notes

Reaction equation

HRID 1475511 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][O:15][CH3:16])[N:11]([CH2:17][C:18]([N:20]2[C:28]3[C:23](=[CH:24][C:25](Br)=[C:26]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][C:31]4=[O:35])[CH:27]=3)[C:22]([CH3:38])([CH3:37])[CH2:21]2)=[O:19])[CH2:10][C@H:9]1[CH3:39])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][O:15][CH3:16])[N:11]([CH2:17][C:18]([N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][C:31]4=[O:35])[CH:27]=3)[C:22]([CH3:38])([CH3:37])[CH2:21]2)=[O:19])[CH2:10][C@H:9]1[CH3:39])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86724039HCID 86724039, compound

Product 1

HCID 70980561HCID 70980561, compoundYield 113.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (12 mg, 0.1 mmol) and (2R,5R)-4-{2-[5-bromo-3,3-dimethyl-6-(2-oxo-pyrrolidin-1-ylmethyl)-2,3-dihydro-indol-1-yl]-2-oxo-ethyl}-5-methoxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (66 mg, 0.1 mmol) were dissolved in methanol (0.44 mL) and triethylamine (23 μL, 0.16 mmol) was added. The reaction was hydrogenated at 1 bar for 1 h at ambient temperature then filtered under vacuum and concentrated. Residue was dissolved in methanol, loaded onto SCX column eluting with methanol then 2.0 M ammonia in methanol to release the amine and the relevant fractions concentrated. Chromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60) gave the title compound (60 mg), MS: [M+H]+=529.

Workup

  1. filtrationthen filtered under vacuum
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in methanol
  4. washeluting with methanol
  5. concentrationthe relevant fractions concentrated
  6. washChromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60)

Sources & evidence

ORD record
ord-a6a53f50da98495fb0ff78bf539e31bd
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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