Triethylamine → HCID 86615459, compound

HRID 1928245Notes

Reaction equation

HRID 1928245 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.C([NH:48][S:49](Cl)(=[O:51])=[O:50])(OC(C)(C)C)=O>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:49]([NH2:48])(=[O:51])=[O:50])[CH:26]=3)[CH:22]=[CH:23][CH:24]=2)[N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 60209449HCID 60209449, compound

Product 1

HCID 86615459HCID 86615459, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3′-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-3-ylamine (example 220) (0.46 g, 1.0 mmol) in dichloromethane (10 mL) was added triethylamine (0.42 mL) and N-Boc-sulfamoyl chloride (0.8M, 3.75 mL, 3.0 mmol), the reaction mixture was allowed to stir at room temperature for 45 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 (dichloromethane/MeOH/hexane) yielded a white solid (0.3 g), which was dissolved in TFA (10 mL) and allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness and saturated NaHCO3 solution (10 mL) was added. The mixture was stirred at room temperature for 30 min, the precipitate was collected by filtration and washed with water. The crude product was further purified by crystallization (dichloromethane/MeOH/hexane) to yield the title compound as a white solid (0.21 g, 39%). MS (ISP) 539.3 [(M+H)+]; mp 174° 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 (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-2d7cfd6b70394f62b4a95a417ee4e9fa
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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