Phthalimide → HCID 178515001, compound

HRID 1852541Notes

Reaction equation

HRID 1852541 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]1([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([NH:35][C@H:36]3[CH2:41][CH2:40][C@H:39]([CH2:42]O)[CH2:38][CH2:37]3)[N:30]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[N:21]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:58]1(=[O:68])[NH:62][C:61](=[O:63])[C:60]2=[CH:64][CH:65]=[CH:66][CH:67]=[C:59]12>C1(C)C=CC=CC=1.O>[N:20]1([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([NH:35][C@H:36]3[CH2:37][CH2:38][C@H:39]([CH2:42][N:62]4[C:58](=[O:68])[C:59]5[C:60](=[CH:64][CH:65]=[CH:66][CH:67]=5)[C:61]4=[O:63])[CH2:40][CH2:41]3)[N:30]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[N:21]1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178520972HCID 178520972, compound

Product 1

HCID 178515001HCID 178515001, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Triphenylphosphine (972 mg, 1.2 eq) was added to a solution of trans-[4-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanol (1 g, 1 equivalent; prepared in a similar manner as described in Example 4) in toluene (100 mL), it was then followed by the dropwise addition of DIAD (0.73 mL, 1.2 eq). The reaction mixture was stirred at RT for 10 minutes and then phthalimide (545 mg, 1.2 eq) was added. The mixture was stirred overnight at RT, water was then added and the resulting mixture was extracted 3 times with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude residue was triturated with MeOH to give 976 mg (70% yield) of trans-2-[4-(4-benzo-triazol-1-yl-pyrimidin-2-ylamino)-cyclohexylmethyl]-isoindole-1,3-dione; MS=454.40 (M+1)+.

Workup

  1. customprepared in a similar manner
  2. stirringThe mixture was stirred overnight at RT
  3. extractionthe resulting mixture was extracted 3 times with EtOAc
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe crude residue was triturated with MeOH

Sources & evidence

ORD record
ord-a6de8ecf3aa340df9c68bf21d1f568d4
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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