Tert-Butylamine → HCID 54281722, compound

HRID 2268620Notes

Reaction equation

HRID 2268620 reaction equation
[C:1]([O:5][C:6]([N:8]([C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[C:15]([N:17](C(C)C(O)=O)[CH:18]1[CH2:21][CH2:20][CH2:19]1)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C([O:44]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)[CH:64]([CH3:66])[CH3:65].[C:70]([NH2:74])([CH3:73])([CH3:72])[CH3:71]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:14]([C:15](=[O:16])[N:17]([CH2:65][CH2:64][C:66](=[O:44])[NH:74][C:70]([CH3:73])([CH3:72])[CH3:71])[CH:18]2[CH2:19][CH2:20][CH2:21]2)[CH:13]=1)[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69950450HCID 69950450, compound

Product 1

HCID 54281722HCID 54281722, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ({3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoyl}-cyclobutyl-amino)-propionic acid (0.025 g) and HATU® (0.038 g) in DMF (1 ml) was added DIPEA (0.017 ml) followed by tert-butylamine (0.053 ml) 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 (0.021 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-62996e515536435baa6af22519aa4d45
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

Loading…