Methanol → HCID 178487817, compound

HRID 2273239Notes

Reaction equation

HRID 2273239 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([C@H:25]1[CH2:30][CH2:29][C@H:28]([N:31]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]2=[O:41])[CH2:27][CH2:26]1)[C:9]([NH:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[OH:22])=[N:19][C:18]([O:23][CH3:24])=[CH:17][CH:16]=2)=[O:10].ClCCl.CO>CN(C)C=O>[CH3:24][O:23][C:18]1[N:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]1[NH:11][C:9](=[O:10])[CH:8]([C@H:25]3[CH2:30][CH2:29][C@H:28]([N:31]4[C:32](=[O:41])[C:33]5[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:39]4=[O:40])[CH2:27][CH2:26]3)[O:22][C:21]2=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 178487955HCID 178487955, compound

Product 1

HCID 178487817HCID 178487817, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.49 g, 18.03 mmol, 3.0 eq) is added at room temperature to a stirred solution of 2-bromo-[trans-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyl]-N-(4-hydroxy-6-methoxy-[1,5]naphthyridin-3-yl)-acetamide (3.24 g, 6.01 mmol, 1.0 eq) in N,N-dimethylformamide (30 mL). After 16 hours stirring at room temperature and 2 hours stirring at 55° C., solvent is removed and the residue is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 2-[trans-4-(6-methoxy-2-oxo-2,3-dihydro-1H-4-oxa-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-isoindole-1,3-dione as a light yellow solid (1.35 g, 49% yield).

Workup

  1. stirringstirring at 55° C.
  2. customsolvent is removed
  3. customthe residue is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-a1f2ff8b0a6349ab93417fd96462352c
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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