Methylamine → HCID 90132499, compound

HRID 2275811Notes

Reaction equation

HRID 2275811 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[O:5][CH2:6][CH:7]([N:20]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN>C(O)C>[NH2:20][CH:7]([CH2:6][O:5][C:4]1[CH:31]=[CH:32][C:33]([F:34])=[C:2]([F:1])[CH:3]=1)[CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 90132498HCID 90132498, compound

Product 1

HCID 90132499HCID 90132499, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

1.8 g of rac-benzyl [3-(3,4-difluorophenoxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-carbamate (Example 139A) were dissolved in 25 ml of ethanol, 4.8 ml of 40% strength aqueous methylamine solution (56 mmol, 15 equivalents) were added and the mixture was stirred at 60° C. for 4.5 h. The reaction mixture was concentrated and the residue was then chromatographed on silica gel (Biotage Isolera; mobile phase: dichloromethane/methanol gradient). This gave 600 mg (45% of theory; purity 93%) 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-da02bcc098f84b3cb5fd8fb54d7f61f8
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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