Diisopropylethylamine → 3-(Isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid methyl ester trifluoroacetate

HRID 2268681Notes

Reaction equation

HRID 2268681 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:17]=1)[C:12]([OH:14])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:59][O:60][C:61](=[O:68])[CH2:62][CH2:63][NH:64][CH:65]([CH3:67])[CH3:66]>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:59][O:60][C:61](=[O:68])[CH2:62][CH2:63][N:64]([CH:65]([CH3:67])[CH3:66])[C:12](=[O:14])[C:11]1[CH:15]=[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:17]=[C:9]([CH3:8])[CH:10]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12774812Methyl 3-[(propan-2-yl)amino]propanoateHCID 699496943-Methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate

Product 1

HCID 699474873-(Isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid methyl ester trifluoroacetateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate (0.025 g) and TBTU (0.021 g) in DMF (1 ml) was added DIPEA (0.022 ml) followed by 3-isopropylamino-propionic acid methyl ester (0.01 g) after 3 min. The reaction was stirred at room temperature for 18 h, and then concentrated under reduced pressure. The residue was subjected to preparative hplc to give the title compound (0.031 g) as a colourless oil, 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-e07a5ad8f0fe446187b3d6f39ccc3a9d
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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