Diisopropylethylamine → HCID 136345880, compound

HRID 2100496Notes

Reaction equation

HRID 2100496 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([NH:15][C:16]1[N:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([NH2:20])=[O:19])=O.CCN(C(C)C)C(C)C>CN(C=O)C>[O:19]=[C:18]1[NH:20][C:13]([CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])=[N:15][C:16]2[N:24]=[CH:23][CH:22]=[CH:21][C:17]1=2

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 68567582HCID 68567582, compound

Product 1

HCID 136345880HCID 136345880, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-nicotinamide (7.24 g, 22.3 mmol) and DIPEA (14.4 ml, 111.6 mmol) in DMF (250 ml) was stirred overnight at 100° C. The reaction mixture was evaporated, redissolved in toluene and brought to dryness under reduced pressure. The residue was triturated with 100 ml EtOAc/MeOH (19/1) and filtrated to yield 2-(4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-ylmethyl)-isoindole-1,3-dione (6.03 g, 19.7 mmol; 88%) as light brown solid. MS (m/e): 307.2 [M+H+].

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionredissolved in toluene
  3. customThe residue was triturated with 100 ml EtOAc/MeOH (19/1)
  4. filtrationfiltrated

Sources & evidence

ORD record
ord-ed31050f062e401da4bd6e3c84820a57
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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