1-Hydroxybenzotriazole → HCID 54289105, compound

HRID 2268603Notes

Reaction equation

HRID 2268603 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]([OH:17])=O)=[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.[CH:69]([NH:72][CH2:73][CH2:74][C:75]1[O:79][N:78]=[C:77]([NH2:80])[N:76]=1)([CH3:71])[CH3:70]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:14]([C:15](=[O:17])[N:72]([CH2:73][CH2:74][C:75]2[O:79][N:78]=[C:77]([NH2:80])[N:76]=2)[CH:69]([CH3:71])[CH3:70])[CH:13]=1)[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)([CH3:4])([CH3:2])[CH3:3]

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 18349096HCID 18349096, compound

Product 1

HCID 54289105HCID 54289105, compoundYield 47.8%

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 (0.104 g), TBTU (0.128 g), and HOBt (0.061 g) in DMF (1 ml) was added DIPEA (0.139 ml) and 5-(2-isopropylamino-ethyl)-[1,2,4]oxadiazol-3-ylamine (0.05 g). The reaction mixture was stirred at room temperature for 10 days, then silica was added and the solvent removed by evaporation at reduced pressure. The resulting silica was loaded onto the top of a column of silica which was then eluted with a gradient [cyclohexane:ethyl acetate (1:1 v/v) to neat ethyl acetate to ethyl acetate:methanol (9:1 v/v)]. Concentration of the required fraction at reduced pressure furnished the title compound as a yellow glass (0.069 g).

Workup

  1. additionsilica was added
  2. customthe solvent removed by evaporation at reduced pressure
  3. washwas then eluted with a gradient [cyclohexane:ethyl acetate (1:1 v/v) to neat ethyl acetate to ethyl acetate:methanol (9:1 v/v)]

Sources & evidence

ORD record
ord-26147954d6624d33bbb3b4d5c8d09908
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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