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

Dimethyl Sulfoxide → HCID 67193954, compound

HRID 1951664
Notes
Print preview

Reaction equation

HRID 1951664 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:22])[C:9](=[O:21])[C:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH:3]=1.[OH:30][C@H:31]1[CH2:35][NH:34][C@H:33]([CH2:36][OH:37])[CH2:32]1.CS(C)=O>C([O-])(O)=O.[Na+]>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:4]1[CH:3]=[C:2]([N:34]2[CH2:35][C@H:31]([OH:30])[CH2:32][C@H:33]2[CH2:36][OH:37])[N:7]=[CH:6][C:5]=1[N:8]([CH3:22])[C:9](=[O:21])[C:10]([C:13]1[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]([Cl:19])[CH:18]=1)([CH3:12])[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 15817396(3R,5S)-5-(Hydroxymethyl)pyrrolidin-3-OLHCID 86597667HCID 86597667, compound

Product 1

HCID 67193954HCID 67193954, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
13 °C

Procedure

To a solution of 0.15 g (0.32 mmol) N-[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3,5-dichloro-phenyl)-N-methyl-isobutyramide and 0.25 g (2.13 mmol) (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine in 2 ml dimethyl sulfoxide 0.2 g (1.55 mmol) Na2CO3 was added and the solution was stirred at 13° C. for 9 h After cooling to ambient temperature, the solution was poured into 20 ml 0.5 N NaHCO3-solution and extracted three times with 30 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 1:2) to give 0.05 g (31%) of the title compound as a white foam. MS m/e (%): 548.3 (M+H+, 100).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted three times with 30 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-3f96e47df24545728113255305571b08
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404708B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes