Triethylamine → HCID 59731947, compound

HRID 1985468Notes

Reaction equation

HRID 1985468 reaction equation
C(OC([C@H:11]1[C:24](=[O:25])[N:23]([CH:26]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]2)[CH2:22][C:14]2[C:15]3[CH:16]=[N:17][NH:18][C:19]=3[CH:20]=[CH:21][C:13]=2[CH2:12]1)=O)C1C=CC=CC=1.[H][H].C(N(CC)CC)C.C1C(=O)[N:51](OC(ON2C(=O)CCC2=O)=O)[C:49](=[O:50])C1.C(O)(=O)C.[NH:69]1[CH2:74][CH2:73][CH:72]([N:75]2[CH2:84][C:83]3[C:78](=[CH:79][CH:80]=[CH:81][CH:82]=3)[NH:77][C:76]2=[O:85])[CH2:71][CH2:70]1>CO.[Pd].ClCCl.C(O)(=O)C>[O:25]=[C:24]1[N:23]([CH:26]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])[CH2:27]2)[CH2:22][C:14]2[C:15]3[CH:16]=[N:17][NH:18][C:19]=3[CH:20]=[CH:21][C:13]=2[CH2:12][C@H:11]1[NH:51][C:49]([N:69]1[CH2:70][CH2:71][CH:72]([N:75]2[CH2:84][C:83]3[C:78](=[CH:79][CH:80]=[CH:81][CH:82]=3)[NH:77][C:76]2=[O:85])[CH2:73][CH2:74]1)=[O:50]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 67318551HCID 67318551, compoundHCID 67318928HCID 67318928, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59731947HCID 59731947, compoundYield 24%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-butyl 3-((R)-7-(benzyloxycarbonyl)-8-oxo-7,8-dihydroazepino[3,4-e]indazol-9(3H,6H,10H)-yl)pyrrolidine-1-carboxylate was dissolved in methanol (10 mL). Acetic acid (300 μL) was added to the mixture followed by 10% palladium on carbon. Reaction vessel was placed on a Parr apparatus and charged with 30 psi of hydrogen gas. Reaction shook at ambient temperature for 2 hours. Reaction mixture was filtered. Filtrate was concentrated in vacuo. Residue was dissolved in dichloromethane (2 mL). Triethylamine (500 μL, 3.6 mmol) was added to the mixture followed by N,N′-disuccinimidyl carbonate (90 mg, 0.35 mmol). Reaction stirred at room temperature for 30 minutes. 3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one acetate (80 mg, 0.27 mmol) was added to the mixture. Reaction stirred at room temperature for 1 hour. Mixture was diluted with dichloromethane. Mixture was washed with water. Organic layer was concentrated. C18 preparative HPLC purification afforded the title compound as yellow solid in 24% yield. MS m/e (M−C5H8O2+H)+=543.

Workup

  1. customReaction vessel
  2. customReaction
  3. customReaction mixture
  4. filtrationwas filtered
  5. concentrationFiltrate was concentrated in vacuo
  6. dissolutionResidue was dissolved in dichloromethane (2 mL)
  7. customReaction
  8. stirringstirred at room temperature for 30 minutes
  9. customReaction
  10. stirringstirred at room temperature for 1 hour
  11. washMixture was washed with water
  12. concentrationOrganic layer was concentrated
  13. customC18 preparative HPLC purification

Sources & evidence

ORD record
ord-07a916cd307d448fb61e3fe0cebcdb2b
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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