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Oxalyl chloride → HCID 54064737, compound

HRID 2268587
Notes
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Reaction equation

HRID 2268587 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([O:11][C:12]([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](O)=[O:22])=[O:13])([CH3:10])([CH3:9])[CH3:8].[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][CH2:42][CH2:43][C:44]#[N:45].CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C.CN(C1C=CN=CC=1)C>[C:7]([O:11][C:12](=[O:13])[N:14]([CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([C:21](=[O:22])[N:41]([CH2:42][CH2:43][C:44]#[N:45])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[F:34])[CH:24]=[C:25]([Cl:27])[CH:26]=1)[C:28]1[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=1)([CH3:10])([CH3:9])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 23805153-[(2-Fluorophenyl)amino]propanenitrileHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 54064737HCID 54064737, compoundYield 34.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

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 1.5 h then a solution of 3-(2-fluoro-phenylamino)propionitrile (0.026 g) in dichloromethane (1 ml), DMAP (0.002 g) and DIPEA (0.078 m l) were added. The reaction mixture was stirred at room temperature for 66 h. The reaction mixture was partitioned between ethyl acetate and 1M aqueous hydrochloric acid. The aqueous layer was removed and the organic phase washed with further 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, water and dried with brine and over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with ethyl acetate:cyclohexane (4:1 v/v), to give the title compound as a colourless gum (0.028 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 66 h
  2. customThe reaction mixture was partitioned between ethyl acetate and 1M aqueous hydrochloric acid
  3. customThe aqueous layer was removed
  4. washthe organic phase washed with further 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, water
  5. dry with materialdried with brine and over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography
  8. washeluting with ethyl acetate:cyclohexane (4:1 v/v)

Sources & evidence

ORD record
ord-257dd14ac0234edba26e69c032d77203
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326386B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes