Dimethylformamide → HCID 18349195, compound

HRID 2268646Notes

Reaction equation

HRID 2268646 reaction equation
[C:1](Cl)(=O)[C:2](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.CC[N:36]([CH:40]([CH3:42])C)[CH:37]([CH3:39])[CH3:38].[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].C[N:51]([CH:53]=[O:54])C>ClCCl.CN(C1C=CN=CC=1)C>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[C:53]([CH2:42][CH2:40][N:36]([C:37]1[CH:38]=[CH:2][CH:1]=[CH:44][CH:39]=1)[C:21](=[O:23])[C:20]1[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]=[C:25]([Cl:27])[CH:24]=1)(=[O:54])[NH2:51]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 18349195HCID 18349195, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2M Oxalyl chloride solution in dichloromethane (0.090 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 (0.059 g) in anhydrous dichloromethane (1 ml). The reaction was stirred at room temperature for 2 h then 3-phenylamino-propionitrile8 (0.027 g), DMAP (0.002 g) and DIPEA (0.078 ml) were added. The reaction mixture was stirred at room temperature for 2 h then trifluoroacetic acid (2 ml) was added and the reaction mixture stirred overnight open to the air. The reaction mixture was concentrated in vacuo and the residue was subjected to preparative hplc. The title compound (0.060 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. stirringThe reaction mixture was stirred at room temperature for 2 h
  2. stirringthe reaction mixture stirred overnight open to the air
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7f63a1c092fd4d0fa37e89e0e434b70d
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

Loading…