N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamide → HCID 117942080, 화합물

HRID 1499102노트

반응식

HRID 1499102 반응식
C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.[Br:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])=[C:30]([N:40]2[CH:44]=[CH:43][C:42]([CH3:45])=[N:41]2)[CH:29]=1.C([O-])=O.[K+]>O.C(#N)C.C[Ir-4](Cl)(C)(C)(C)(C)C1C=CC=C1>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]([OH:39])[C:35]([F:38])([F:37])[F:36])=[C:30]([N:40]2[CH:44]=[CH:43][C:42]([CH3:45])=[N:41]2)[CH:29]=1

참가 물질

7

반응물 3

HCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideHCID 2735122Potassium FormateHCID 1179421121-(4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone

생성물 1

HCID 117942080HCID 117942080, 화합물

시약·촉매·용매 3

HCID 178477776HCID 178477776, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

Pentamethylcyclopentadienyl iridium (III) chloride dimer (CAS#12354-84-6) (10.4 mg) and (1R,2R)-(−)-N-(4-toluene sulfonyl)-1,2-diphenyl ethylene diamine (CAS#144222-34-4) (9.2 mg) were combined in water (120 mL), then heated to 50° C. for 5 h to provide the “Iridium complex.” 1-[4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethanone (16 g, 48 mmol) was dissolved in acetonitrile (120 mL) to which the Iridium complex and potassium formate (3.1 g, 3.7 mmol) were added. The reaction mixture was heated to 50° C. for 8 h. The reaction mixture was then cooled to RT, partitioned between water and EtOAc, and extracted. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Recrystallization from hot heptane (200 mL) provided the title compound.

후처리

  1. customto provide the “Iridium complex
  2. additionwere added
  3. temperatureThe reaction mixture was heated to 50° C. for 8 h
  4. temperatureThe reaction mixture was then cooled to RT
  5. custompartitioned between water and EtOAc
  6. extractionextracted
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customRecrystallization from hot heptane (200 mL)

출처 및 근거

ORD 기록
ord-89e44f85a3e4496ca1b80e58d5cb93fa
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199994B2

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