Water → HCID 58959680, compound

HRID 2353179Notes

Reaction equation

HRID 2353179 reaction equation
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3.C(N(CC)CC)C.C([N:45]1[CH2:52][CH2:51][CH2:50][C@H:46]1[C:47](Cl)=[O:48])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.O>CN(C=O)C.N1CCCCC1>[O:20]=[C:17]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[O:13][C:14]4[CH:15]=[CH:16][C:3]([CH2:2][NH:1][C:47]([CH:46]5[CH2:50][CH2:51][CH2:52][NH:45]5)=[O:48])=[CH:4][C:5]=4[C:6]([C:7]=23)=[N:19][NH:18]1

Participants

7

Reactant 4

HCID 962Water2×HCID 8471TriethylamineHCID 111003579H-Fluoren-9-ylmethyl (2S)-2-(chlorocarbonyl)-1-pyrrolidinecarboxylateHCID 1119635510-(Aminomethyl)[1]benzopyrano[4,3,2-de]phthalazin-3(2H)-one

Product 1

HCID 58959680HCID 58959680, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8082PiperidineSolvent

Procedure

To a solution of compound 49 (0.5 mmol) in DMF was added triethylamine (0.6 mmol) and Fmoc-L-Proline chloride (0.6 mmol) slowly. The reaction mixture was stirred at room temperature for 3 hours. Water was poured into the reaction mixture. A white precipitate was formed and collected through filtration. The white solid was recrystallized to afford a white solid in 65% yield. The white solid was dissolved in 20% piperidine in DMF. The solution was stirred at room temperature for 2 hours. Water was added to the solution. Aqueous layer was extracted with ethyl acetate. Organic layer was collected, washed with brine, and dried. Solvent was removed to afford a white solid 53 in 54% yield. MS (ES+): 363; 1H-NMR (DMSO-d6, 400 MHz): 12.64 (s, 1H), 8.59 (t, J=5.8 Hz, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.90-7.82 (m, 2H), 7.72 (dd, J=7.5 and 2.0 Hz, 1H), 7.43 (dd, J=8.5 and 2.0 Hz, 1H), 7.36 (d, J=8.5 Hz, 1H), 4.35 (d, J=3.8 Hz, 2H), 3.62 (m, 1H), 2.98 (t, J=5.2 Hz, 1H), 2.87 (m, 1H), 1.99 (m, 1H), 1.73 (m, 1H), 1.64 (m, 2H); Anal. Calcd. for C20H18N4O3.(1.2H2O): C, 62.56; H, 5.35; N, 14.59. Found: C, 62.75; H, 5.34; N, 14.52.

Workup

  1. customA white precipitate was formed
  2. filtrationcollected through filtration
  3. customThe white solid was recrystallized
  4. customto afford a white solid in 65% yield
  5. stirringThe solution was stirred at room temperature for 2 hours
  6. extractionAqueous layer was extracted with ethyl acetate
  7. customOrganic layer was collected
  8. washwashed with brine
  9. customdried
  10. customSolvent was removed

Sources & evidence

ORD record
ord-39474c05ba264148b3b3cae249fd7ae8
Source dataset
uspto-grants-2010_07
Patent number
US07750008B2

Reaction notes

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