Methylamine → HCID 90136028, compound

HRID 2275792Notes

Reaction equation

HRID 2275792 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([CH2:22][O:23][CH2:24][CH3:25])[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].CN>>[NH2:3][CH:12]([CH2:22][O:23][CH2:24][CH3:25])[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 90136000HCID 90136000, compound

Product 1

HCID 90136028HCID 90136028, compound

Procedure

4.88 g of rac-tert-butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-ethoxypropyl]carbamate (14.0 mmol, 1 equivalent) were initially charged in 12 ml of 40% strength aqueous methylamine solution and reacted in a microwave at 100° C. for 1.5 h. The reaction mixture was concentrated, the residue was taken up in 10 ml of toluene and concentrated again. This step was repeated several times. The residue was then chromatographed on silica gel (mobile phase: dichloromethane/methanol 10:1). This gave 470 mg (15% of theory) of the title compound.

Workup

  1. customreacted in a microwave at 100° C. for 1.5 h
  2. concentrationThe reaction mixture was concentrated
  3. concentrationconcentrated again
  4. customThe residue was then chromatographed on silica gel (mobile phase: dichloromethane/methanol 10:1)

Sources & evidence

ORD record
ord-234ff1029bc0429490cb03bd39ba7559
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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