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Oxalyl chloride → HCID 53935279, compound

HRID 2268596
Notes
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Reaction equation

HRID 2268596 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].[C:34]1([NH:40][CH2:41][CH2:42][S:43]([F:46])(=[O:45])=[O:44])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.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:40]([CH2:41][CH2:42][S:43]([F:46])(=[O:45])=[O:44])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:24]=[C:25]([Cl:27])[CH:26]=1)[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)([CH3:9])([CH3:8])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 125534362-Anilinoethane-1-sulfonyl fluorideHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 53935279HCID 53935279, compoundYield 54.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

2M Oxalyl chloride solution in dichloromethane (0.9 ml) and DMF (0.025 ml) were added to a suspension of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.610 g) in anhydrous dichloromethane (50 ml). The reaction was stirred at room temperature for 1 h then 2-phenylamino-ethanesulfonyl fluoride(0.257 g), DMAP (0.018 g) and DIPEA (0.261 ml) were added. The reaction mixture was stirred at room temperature for 20 h and partitioned between ethyl acetate and 1M aqueous hydrochloric acid. The aqueous layer was removed and the organic phase washed with saturated aqueous sodium bicarbonate, water and dried with brine and over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with using ethyl acetate:petroleum ether (3:1 v/v) to give the title compound as a white foam (0.40 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 h
  2. custompartitioned between ethyl acetate and 1M aqueous hydrochloric acid
  3. customThe aqueous layer was removed
  4. washthe organic phase washed with saturated aqueous sodium bicarbonate, 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 using ethyl acetate:petroleum ether (3:1 v/v)

Sources & evidence

ORD record
ord-4fc8f36d09a449e7b16f24282b5d1540
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