HCID 55290937, compound → HCID 11235018, compound

HRID 2251853Notes

Reaction equation

HRID 2251853 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3OS(C(F)(F)F)(=O)=O)[CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[C:33]([NH:37][CH3:38])[N:32]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:12][C:13]3[C:18](=[C:17]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][N:34]=[C:33]([NH:37][CH3:38])[N:32]=4)[CH:16]=[CH:15][CH:14]=3)[C:19]2=[O:20])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 55290937HCID 55290937, compoundHCID 86596911HCID 86596911, compound

Product 1

HCID 11235018HCID 11235018, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

Trifluoromethanesulfonic acid 2-(4-t-butyl-phenyl)-3-oxo-2,3-dihydro-1H-isoindol-4-yl ester (42 mg, Step A), (4-aminomethyl-pyrimidin-2-yl)-methyl-amine (19.2 mg), Pd(OAc)2 (3.4 mg), dppf (9.5 mg), CeCO3 (70 mg) and toluene (1 mL) were put into a microwave reaction tube and subjected to 120° C., for a total of 55 min of microwave. The solid was removed by filtration and solvent was evaporated. The resulting residue was purified by Gilson HPLC purification system to obtain 2-(4-t-butyl-phenyl)-7-[(2-methylamino-pyrimidin-4-ylmethyl)-amino]-2,3-dihydro-isoindol-1-one.

Workup

  1. customsubjected to 120° C., for a total of 55 min of microwave
  2. customThe solid was removed by filtration and solvent
  3. customwas evaporated
  4. customThe resulting residue was purified by Gilson HPLC purification system

Sources & evidence

ORD record
ord-1ed72046f1bc40468d84a917d1ec6b51
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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