HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Oxalyl chloride → 3-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide

HRID 1366797
Notes
Print preview

Reaction equation

HRID 1366797 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:14]=2[S:13][C:12]=1[C:20](O)=[O:21].C(Cl)(=O)C(Cl)=O.[CH:29]([O:31][CH2:32][CH2:33][O:34][NH2:35])=[CH2:30].CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[CH:29]([O:31][CH2:32][CH2:33][O:34][NH:35][C:20]([C:12]1[S:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[C:11]=1[NH:10][C:3]1[CH:4]=[CH:5][C:6]([S:8][CH3:9])=[CH:7][C:2]=1[F:1])=[O:21])=[CH2:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 597039013-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid

Product 1

HCID 597038883-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amideYield 18%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 3-(2-fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (0.107 g, 0.32 mmol) in dry dichloromethane (5 ml) under an atmosphere of nitrogen was cooled to 0° C. and treated with DMF (1 drop) and oxalyl chloride (0.081 ml, 0.96 mmol). The reaction mixture was stirred for 1 hour then the solvent removed in vacuo. The resultant residue was re-suspended in dry dichloromethane (1 ml) and treated dropwise with a solution of O-(2-vinyloxy-ethyl) -hydroxylamine (0.066 g, 0.64 mmol) and DIPEA (0.167 ml, 0.96 mmol) in dry dichloromethane (4 ml) before being stirred for 18 hours. The reaction mixture was washed (water, brine), dried (MgSO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si-SPE, gradient 0-30% ethyl acetate in dichloromethane) to provide the title compound as a yellow solid (0.024 g, 18%). LCMS (method B): RT=3.17 min, M+H+ 420.

Workup

  1. customthe solvent removed in vacuo
  2. stirringbefore being stirred for 18 hours
  3. washThe reaction mixture was washed (water, brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25a59f44cc0a45b19b79d5c6d7cc2410
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07893085B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes