Methylamine → HCID 90136020, compound

HRID 2275799Notes

Reaction equation

HRID 2275799 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([CH2:25][O:26][CH:27]([CH3:29])[CH3:28])[CH2:13][NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN>C(O)C>[NH2:3][CH:12]([CH2:25][O:26][CH:27]([CH3:29])[CH3:28])[CH2:13][NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 90136015HCID 90136015, compound

Product 1

HCID 90136020HCID 90136020, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2.3 g of rac-benzyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-isopropoxypropyl]carbamate (5.6 mmol, 1 equivalent) were dissolved in 30 ml of ethanol, 7.3 ml of 40% strength aqueous methylamine solution (84.4 mmol, 15 equivalent) were added and the mixture was stirred at 60° C. overnight. The reaction mixture was concentrated and the residue was then chromatographed on silica gel (Biotage Isolera; mobile phase: dichloromethane/methanol gradient). This gave 730 mg (49% of theory) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was then chromatographed on silica gel (Biotage Isolera; mobile phase: dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-6ff07479a06141db929e6d6bde54de3d
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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