1-Hydroxybenzotriazole → HCID 54359784, compound

HRID 2268579Notes

Reaction equation

HRID 2268579 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:15](O)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:69]([O:71][C:72](=[O:82])[CH2:73][CH2:74][CH2:75][NH:76][CH:77]1[CH2:81][CH2:80][CH2:79][CH2:78]1)[CH3:70]>CN(C=O)C>[CH2:69]([O:71][C:72](=[O:82])[CH2:73][CH2:74][CH2:75][N:76]([C:15](=[O:16])[C:14]1[CH:18]=[C:19]([Cl:21])[CH:20]=[C:12]([O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:13]=1)[CH:77]1[CH2:81][CH2:80][CH2:79][CH2:78]1)[CH3:70]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-HCID 54374707HCID 54374707, compound2×

Product 1

HCID 54359784HCID 54359784, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.300 g), TBTU (0.482 g) and HOBt (0.150 g) in DMF (5 ml) was added DIPEA (0.260 ml) followed by 4-cyclopentylamino-butyric acid ethyl ester (0.316 g) after 10 min. The reaction mixture was stirred at room temperature for 16 h and then further 4-cyclopentylamino-butyric acid ethyl ester (0.316 g) was added. After 24 h, the reaction mixture was concentrated under reduced pressure to give a viscous gum which was partitioned between ethyl acetate and water. The aqueous layer was removed and the organic phase washed with further water, aqueous saturated sodium bicarbonate solution, water and dried with brine and over sodium sulphate. The organic phase was concentrated under reduced pressure to give crude product as a black gum (0.420 g) which was purified by preparative hplc and the title compound (0.189 g) was obtained as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. waitAfter 24 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto give a viscous gum which
  4. customwas partitioned between ethyl acetate and water
  5. customThe aqueous layer was removed
  6. washthe organic phase washed with further water, aqueous saturated sodium bicarbonate solution, water
  7. dry with materialdried with brine and over sodium sulphate
  8. concentrationThe organic phase was concentrated under reduced pressure
  9. customto give crude product as a black gum (0.420 g) which
  10. customwas purified by preparative hplc

Sources & evidence

ORD record
ord-dd3b34bd636441a1ba465bef23cc95c0
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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