1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 68429263, compound

HRID 2092104Notes

Reaction equation

HRID 2092104 reaction equation
[Br:1][C:2]1[C:3](=[O:19])[NH:4][N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][N:29]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]1=[O:39].[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:19])[N:4]([CH2:27][CH2:28][N:29]2[C:30](=[O:39])[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:37]2=[O:38])[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:16])[CH3:17])[C@H:10]1[CH3:18]

Participants

6

Reactant 4

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 68429305HCID 68429305, compound

Product 1

HCID 68429263HCID 68429263, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (100 mg, 0.306 mmol) and potassium carbonate (51 mg, 0.0369 mmol) in N,N-dimethylformamide (3 mL) were stirred with 2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione (93 mg, 0.366 mmol) at 80° C. for 7 hours. After completion of the reaction, the reaction solution was mixed with aqueous ammonium chloride and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was used for the next reaction without purification.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was used for the next reaction without purification

Sources & evidence

ORD record
ord-9cd2e1cc6b6d440e9a67c146e3df0832
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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