1-Hydroxybenzotriazole → HCID 53884199, compound

HRID 2268582Notes

Reaction equation

HRID 2268582 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].C[N:29]([C:31]([O:35]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:50]1C=CC2N(O)N=NC=2[CH:55]=1.CC[N:62]([CH:66]([CH3:68])[CH3:67])[CH:63]([CH3:65])C>CN(C=O)C.C1(NCCC(N)=O)CCCC1>[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:62]([CH2:63][CH2:65][C:31](=[O:35])[NH2:29])[CH:66]2[CH2:67][CH2:55][CH2:50][CH2:68]2)[CH:13]=1)[C:22]1[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

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]-

Product 1

HCID 53884199HCID 53884199, compound

Reagents, catalysts & solvents 2

HCID 18349113HCID 18349113, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-[2-(tert-butoxycarbonyl-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 3-cyclopentylamino-propionamide (0.047 mg) 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 (0.074 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-f20c5b6c6a6a4ab999b3ea20609f97b8
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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