Diisopropylethylamine → HCID 178490378, compound

HRID 1855652Notes

Reaction equation

HRID 1855652 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.[C:56]([NH:60][C:61]([C:63]1([CH:69]2[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]2)[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1)=[O:62])([CH3:59])([CH3:58])[CH3:57]>ClCCl.CN(C)C=O>[C:56]([NH:60][C:61]([C:63]1([CH:69]2[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]2)[CH2:64][CH2:65][N:66]([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)[CH2:67][CH2:68]1)=[O:62])([CH3:59])([CH3:57])[CH3:58]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18418943HCID 18418943, compoundHCID 178490381HCID 178490381, compound

Product 1

HCID 178490378HCID 178490378, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 150 mg (0.45 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxy-phenyl)propanoic acid dissolved in 3 ml of dichloromethane and 0.5 ml of dimethylformamide are added 0.16 ml (0.90 mmol) of diisopropylethylamine, 161 mg (0.50 mmol) of TBTU and 133 mg (0.50 mmol) of 4-tert-butylcarbamoyl-4-cyclohexylpiperidine. 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: dichloromethane/methanol 85/15). 29 mg of 4-tert-butylcarbamoyl 4-cyclohexyl-1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]-piperidine in the form of a white powder are obtained in a yield of 11%.

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: dichloromethane/methanol 85/15)

Sources & evidence

ORD record
ord-28232b896f5244faa835e422047621cb
Source dataset
uspto-grants-2015_02
Patent number
US08962846B2

Reaction notes

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