Pyrrolidine → HCID 54085301, compound

HRID 2268590Notes

Reaction equation

HRID 2268590 reaction equation
[C:1]([O:5][C:6]([N:8]([C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:31]=[C:32]([Cl:34])[CH:33]=1)[C:15]([N:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(O[N:49]1N=NC2C=[CH:53][CH:54]=[CH:55][C:50]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.N1CCCC1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15](=[O:16])[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[CH2:18][CH2:19][CH2:20][C:21](=[O:23])[N:49]2[CH2:50][CH2:55][CH2:54][CH2:53]2)[CH:31]=[C:32]([Cl:34])[CH:33]=1)[C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18349000HCID 18349000, compound

Product 1

HCID 54085301HCID 54085301, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-({3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoyl}-(2-fluoro-phenyl)-amino)-butyric acid (0.025 g), TBTU (0.028 g) and HOBt (0.012 g) in DMF (1 ml) was added DIPEA (0.015 ml) followed by pyrrolidine (0.007 ml) after 10 min. The reaction mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.025 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-ff882d9d784444aab50d7fc41cc18155
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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