1,2-Dichloroethane → HCID 10297462, compound

HRID 584129Notes

Reaction equation

HRID 584129 reaction equation
N(CCCC(OC)=O)=[N+]=[N-].C(C1C=CC(OC)=CC=1)#C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:30]=[N:31][N:32]([CH2:34][CH2:35][C:36]([OH:38])=O)[CH:33]=2)=[CH:25][CH:24]=1.[NH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:47](=[O:54])[NH:46][N:45]=1.C(Cl)CCl.C(N(CC)CC)C>O1CCOCC1.CN(C=O)C>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[N:30]=[N:31][N:32]([CH2:34][CH2:35][C:36]([NH:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]3[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:47](=[O:54])[NH:46][N:45]=3)=[O:38])[CH:33]=2)=[CH:27][CH:28]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 2510201-Ethynyl-4-methoxybenzeneHCID 111486744-(3-amino-propylamino)-2H-phthalazin-1-oneHCID 11218847HCID 11218847, compoundHCID 13202491Methyl 4-azidobutanoate

Product 1

HCID 10297462HCID 10297462, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
175 °C

Procedure

Methyl 4-azidobutyrate (200 mg, 1.40 mmol) and 1-ethynyl-4-methoxybenzene (277 mg, 210 mmol) were dissolved in dioxane (3 mL) and heated in a microwave reactor for 5 min at 175° C. The reaction mixture was filtered and the filtrate was concentrated under vacuum. Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid methyl ester was treated with aqueous 2M NaOH (5 mL) in THF (3 mL) and stirred at RT for 5 h. The methanol was removed under vacuum and the residue was dissolved in dioxane (5 mL) and treated with concentrated HCl dropwise until a precipitate formed. The resulting acid was collected by filtration and the purity was measured by RPLC (78%). Compound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid (125 mg, 0.50 mmol) and 4-(3-amino-propylamino)-2H-phthalazin-1-one (100 mg, 0.46 mmol) were dissolved in DMF (2 mL) and treated with EDC (95 mg, 0.50 mmol) and triethylamine (76 mg, 0.75 mmol). 3-[4-(4-Methoxy-phenyl)-[1,2,3]triazol-1-yl]-N-[3-(4-oxo-3,4-dihydro-phthalazin-1-ylamino)-propyl]-propionamide was isolated by preparative RPLC.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. additionCompound 3-[4-(4-methoxy-phenyl)-[1,2,3]triazol-1-yl]-propionic acid methyl ester was treated with aqueous 2M NaOH (5 mL) in THF (3 mL)
  4. customThe methanol was removed under vacuum
  5. dissolutionthe residue was dissolved in dioxane (5 mL)
  6. additiontreated with concentrated HCl dropwise until a precipitate
  7. customformed
  8. filtrationThe resulting acid was collected by filtration

Sources & evidence

ORD record
ord-172e22f21c0a41459aff890c3b8e969d
Source dataset
uspto-grants-2005_08
Patent number
US06924284B2

Reaction notes

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