Methylamine → HCID 90136002, compound

HRID 2275796Notes

Reaction equation

HRID 2275796 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[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][C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 90136018HCID 90136018, compound

Product 1

HCID 90136002HCID 90136002, compound

Procedure

1.97 g of rac-tert-butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-fluorophenoxy)propyl]-carbamate (4.75 mmol, 1 equivalent) were initially charged in 5 ml of 40% strength aqueous methylamine solution, and the mixture was reacted in a microwave at 100° C. for 2 h. The reaction mixture was concentrated and the residue was then chromatographed on silica gel (Biotage Isolera; mobile phase: dichloromethane/methanol gradient). This gave 900 mg (67% of theory) of the title compound.

Workup

  1. customthe mixture was reacted in a microwave at 100° C. for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was then chromatographed on silica gel (Biotage Isolera; mobile phase: dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-243ab2736e24400ca1bbaeea9650960e
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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