Water → 1,3-Dihydro-isoindole-2-carboxylicacid[4-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-yl)-phenyl]-amide

HRID 624158Notes

Reaction equation

HRID 624158 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:11](=[O:18])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[O:19]=[C:20]1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O.[CH2:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][NH:38]1.O>CN(C)C=O.C(O)C>[O:18]=[C:11]1[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=2[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:20]([N:38]3[CH2:39][C:40]4[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:37]3)=[O:19])=[CH:7][CH:6]=2)=[N:9][NH:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 422478IsoindolineHCID 676246Di(succinimido) carbonateHCID 68750341HCID 68750341, compound

Product 1

HCID 575099931,3-Dihydro-isoindole-2-carboxylicacid[4-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-yl)-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 200 mg 4-(4-aminophenyl)-5,6,7,8-tetrahydro-2H-phthalazin-1-one (0.829 mmol) in 5 ml N,N-dimethylformamide were added 245 mg carbonic acid bis-(2,5-dioxo-pyrrolidin-1-yl) ester (0.912 mmol) and the reaction mixture was stirred overnight. 255 mg of isoindoline were added, the precipitation formed was dissolved by adding 0.8 ml N,N-dimethylformamide, and the reaction mixture was stirred overnight. Water was added, and the formed precipitation was washed with water/methanol and subsequently dried in vacuum to obtain the crude material. The crude material was refluxed in 20 ml ethanol for 2 hours, cooled to room temperature, filtered and dried to obtain the desired product. ESI-MS [M+H+]=387.2.

Workup

  1. customthe precipitation
  2. customformed
  3. dissolutionwas dissolved
  4. stirringthe reaction mixture was stirred overnight
  5. customthe formed precipitation
  6. washwas washed with water/methanol
  7. customsubsequently dried in vacuum
  8. customto obtain the crude material
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-1a1c760112e44a978b75f43f2fb4dd66
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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