Ammonia → HCID 54185563, compound

HRID 2268581Notes

Reaction equation

HRID 2268581 reaction equation
[C:1]([O:5][C:6]([N:8]([C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:29]=[C:30]([Cl:32])[CH:31]=1)[C:15]([N:17]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)[CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:40](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.N>CN(C=O)C.O1CCOCC1>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:31]=[C:30]([Cl:32])[CH:29]=[C:14]([C:15](=[O:16])[N:17]([CH2:18][CH2:19][CH2:20][C:21](=[O:22])[NH2:40])[CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:13]=1)[C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18348884HCID 18348884, compound

Product 1

HCID 54185563HCID 54185563, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4-({3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoyl}-cyclopentyl-amino)-butyric acid (0.049 g), TBTU (0.058 g) and HOBt (0.024 g) in DMF (1 ml) was added DIPEA (0.031 ml) followed a 0.5M solution of ammonia in 1,4-dioxane (0.36 ml) after 15 min. The reaction mixture was stirred at room temperature for 43 h and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.040 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. customafter 15 min
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e32aa19dcb649f0a19f5ad5c0c7d570
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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