Triethylamine → HCID 57468594, compound

HRID 1989527Notes

Reaction equation

HRID 1989527 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][S:42](Cl)(=[O:44])=[O:43].C([O-])(O)=O.[Na+]>ClCCl>[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:42]([CH3:41])(=[O:44])=[O:43])[CH:26]=3)[CH:22]=[CH:23][CH:24]=2)[N:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 60209449HCID 60209449, compound

Product 1

HCID 57468594HCID 57468594, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (ice bath) solution of 3′-[4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyrimidin-2-yl]-biphenyl-3-ylamine (example 220) (0.23 g, 0.5 mmol) in dichloromethane (5 mL) was added triethylamine (0.21 mL) and methanesulfonyl chloride (0.06 g, 0.52 mmol), the reaction mixture was allowed to stir at room temperature for 1 h, poured into sat. NaHCO3 solution (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 (dichloromethane/MeOH/hexane) yielded the title compound (0.16 g, 72%) as a white solid. MS (ISP) 538.0 [(M+H)+]; mp 191° C.

Workup

  1. stirringto stir at room temperature for 1 h
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customFurther purification by flash chromatography
  7. customon silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-ca6f4dd9b3b64cd287d7a514ca249d91
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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