Trifluoroacetic acid → HCID 18348838, compound

HRID 2268645Notes

Reaction equation

HRID 2268645 reaction equation
C(Cl)(=O)C(Cl)=O.C(OC([N:14]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[C:21]([OH:23])=O)=O)(C)(C)C.[CH2:34]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[F:43])[CH3:35].CCN(C(C)C)C(C)C.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56]>ClCCl.CN(C=O)C>[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].[Cl:27][C:25]1[CH:24]=[C:20]([CH:19]=[C:18]([O:17][CH2:16][CH2:15][NH:14][C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)[CH:26]=1)[C:21]([N:36]([CH2:34][CH3:35])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[F:43])=[O:23]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2737180N-ethyl-2-fluoroanilineHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 18348838HCID 18348838, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

2M Oxalyl chloride solution in dichloromethane (0.080 ml) and DMF (0.001 ml) were added to a suspension of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.050 g) in anhydrous dichloromethane (1 ml). The reaction was stirred at room temperature for 2 h then a solution of N-ethyl-2-fluoroaniline (0.029 g) DMAP (0.001 g) and DIPEA (0.070 ml) were added. The reaction mixture was stirred at room temperature for 16 h and then triflouroacetic acid (1 ml) was added. The solvent was removed in vacuo, the residue was subjected to preparative hplc and the required fraction dried by repetitive addition of acetonitrile and concentration under reduced pressure to give the title compound (0.020 g) as a colourless gum.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. customThe solvent was removed in vacuo
  3. dry with materialthe required fraction dried by repetitive addition of acetonitrile and concentration under reduced pressure

Sources & evidence

ORD record
ord-035ef78554b34ae3b932c461930edf24
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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