1-Hydroxybenzotriazole → HCID 54024944, compound

HRID 2268578Notes

Reaction equation

HRID 2268578 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(O[N:36]1N=N[C:38]2[CH:39]=CC=C[C:37]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(N[CH:73]1[CH2:78][CH2:77][CH2:76][CH2:75][O:74]1)CC>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15](=[O:17])[N:36]([CH2:37][CH2:38][CH3:39])[CH:77]2[CH2:78][CH2:73][O:74][CH2:75][CH2:76]2)[CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)([CH3:2])([CH3:4])[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 18349155HCID 18349155, compound

Product 1

HCID 54024944HCID 54024944, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.06 g), TBTU (0.096 g) and HOBt (0.030 g) in DMF (1 ml) was added DIPEA (0.052 ml) followed by N-propyl-aminotetrahydropyran (0.033 g) as a solution in DMF (1 ml) after 20 min. The reaction mixture was stirred at room temperature for 20 h and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with further water and saturated aqueous sodium bicarbonate and dried with brine and over sodium sulphate and concentrated under reduced pressure to give the title compound as a gum (0.07 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with further water and saturated aqueous sodium bicarbonate
  4. dry with materialdried with brine and over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e7ad7e443fc4d999c8c4f211816ebd5
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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