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Triethylamine → HCID 86615460, compound

HRID 1989526
Notes
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Reaction equation

HRID 1989526 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:6]=[C:5]([C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=3)[CH:22]=[CH:23][CH:24]=2)[N:4]=1.C(N(CC)CC)C.[CH3:41][N:42]([CH3:47])[S:43](Cl)(=[O:45])=[O:44]>C1(C)C=CC=CC=1>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:6]=[C:5]([C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][S:43]([N:42]([CH3:47])[CH3:41])(=[O:45])=[O:44])[CH:26]=3)[CH:22]=[CH:23][CH:24]=2)[N:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 60209449HCID 60209449, compound

Product 1

HCID 86615460HCID 86615460, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3′-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-3-ylamine (example 220) (0.23 g, 0.5 mmol) in toluene (5 mL) was added triethylamine (0.21 mL) and dimethylsulfamoyl chloride (0.14 g, 1.0 mmol), the reaction mixture was allowed to stir at 70° C. for 22 h, poured into ice-water (20 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated. Further purification by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (EtOH/hexane) yielded the title compound (0.104 g, 37%) as an off-white solid. MS (ISP) 567.3 [(M+H)+]; mp 113° C.

Workup

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. washThe combined organic layers were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customFurther purification by flash chromatography
  6. customon silica gel (ethyl acetate/heptane) and crystallization (EtOH/hexane)

Sources & evidence

ORD record
ord-04ac12f98573450ab0627ceef84a2d5d
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07642264B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes