Phthalimide → HCID 21076931, compound

HRID 1455161Notes

Reaction equation

HRID 1455161 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C(N1C(=O)[C:23]([CH3:26])=[C:22]([CH3:27])[N:21]=[C:20]1[C@H:28]([N:32]([CH2:42][CH2:43][N:44]1C(=O)C2C(=CC=CC=2)C1=O)[C:33](=O)[C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1)[CH:29]([CH3:31])[CH3:30])C1C=CC=CC=1.O.NN>C(O)C>[CH2:4]([N:5]1[C:1](=[O:11])[C:23]([CH3:26])=[C:22]([CH3:27])[N:21]=[C:20]1[C@H:28]([N:32]1[CH2:42][CH2:43][N:44]=[C:33]1[C:34]1[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=1)[CH:29]([CH3:31])[CH3:30])[C:3]1[CH:2]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 24654Hydrazine hydrate (1:1)HCID 69016795HCID 69016795, compound

Product 1

HCID 21076931HCID 21076931, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

The phthalimide protected amine, N—[(R)-1-(1-benzyl-4,5-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-N-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-4-methyl-benzamide, (0.075 g, 0.13 mMol) was treated with hydrazine monohydrate (0.013 mL, 0.26 mMol) in ethanol (1 mL) at 70° C. for 12 h. The reaction was filtered, concentrated under vacuum and dissolved in toluene (1 mL) and heated to 120° C. for 20 h. The reaction was concentrated under vacuum, taken up in CH3CN and purified by reverse phase HPLC (YMC, ODS-A, 20 min, 5-90% gradient, CH3CN:H2O, 0.1% TFA) The fractions were collected and evaporated to give the title compound as a clear oil. (0.016 g): MS (ES) m/e 429.4 (M+H)+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated under vacuum
  3. dissolutiondissolved in toluene (1 mL)
  4. concentrationThe reaction was concentrated under vacuum
  5. custompurified by reverse phase HPLC (YMC, ODS-A, 20 min, 5-90% gradient, CH3CN:H2O, 0.1% TFA) The fractions
  6. customwere collected
  7. customevaporated

Sources & evidence

ORD record
ord-16e3537473fc4b71b1c47b4318959f9b
Source dataset
uspto-grants-2009_01
Patent number
US07482343B2

Reaction notes

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