Diisopropylethylamine → HCID 178450015, compound

HRID 333413Notes

Reaction equation

HRID 333413 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.FC(F)(F)C(O)=O.[CH2:63]([O:67][C:68]1([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[CH2:71][NH:70][CH2:69]1)[CH2:64][CH2:65][CH3:66]>ClCCl.CN(C)C=O>[CH2:63]([O:67][C:68]1([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[CH2:71][N:70]([C:12](=[O:14])[CH:11]([NH:10][C:9]([NH:8][CH2:7][CH2:6][C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[O:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:69]1)[CH2:64][CH2:65][CH3:66]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669880053-Butoxy-3-phenylazetidine trifluoroacetateHCID 178490381HCID 178490381, compound

Product 1

HCID 178450015HCID 178450015, compoundYield 3.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 57 mg (0.17 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)-propanoic acid (cf. preparation 2-3) dissolved in 4 mL of dichloromethane and 1.5 mL of dimethylformamide are added 0.12 mL (0.68 mmol) of diisopropylethylamine, 61 mg (0.19 mmol) of TBTU and 55 mg (0.17 mmol) of 3-butoxy-3-phenylazetidine trifluoroacetate. After 3 hours, the solution is washed with 1N sodium hydroxide solution and the organic products are extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product obtained is purified by preparative TLC (eluent: 9/1 dichloromethane/methanol). 3 mg of 1-[2-(3-butoxy-3-phenylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-3-[2-(1H-imidazol-4-yl)ethyl]urea are obtained in a yield of 3%.

Workup

  1. washthe solution is washed with 1N sodium hydroxide solution
  2. extractionthe organic products are extracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customis purified by preparative TLC (eluent: 9/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-afab8191d9de4c83a9c281e628888260
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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