1-Hydroxybenzotriazole → HCID 69950514, compound

HRID 2268583Notes

Reaction equation

HRID 2268583 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(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=[CH:40][CH:41]=[CH:42][C:37]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:50]1[CH:51]=CC2N(O)N=NC=2[CH:55]=1.[CH3:60][CH2:61][N:62]([CH:66]([CH3:68])C)[CH:63]([CH3:65])[CH3:64].C1(NCC(N)=[O:77])CCCC1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:40]=[CH:41][CH:42]=[CH:37][C:13]=1[CH:14]1[CH:68]([C:66](=[O:77])[N:62]([CH2:61][CH3:60])[C:63]2[CH:64]=[CH:51][CH:50]=[CH:55][CH:65]=2)[CH2:20][CH:19]([Cl:21])[CH2:18]1)[C:22]1[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=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 167782572-(Cyclopentylamino)acetamideHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 69950514HCID 69950514, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-[2-(tert-butoxy carbonyl-pyridin-4-yl-amino)-ethoxy-]-5-chloro-benzoic acid (0.060 g), TBTU (0.096 g) and HOBt (0.030 g) in DMF (1 ml) was added DIPEA (0.052 ml) followed by 2-cyclopentylamino-acetamide (0.043 g) after 10 min. The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.064 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. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0c29b0831274e208bbafa6783ca2562
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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