Hydrochloric Acid → HCID 86693890, 화합물

HRID 404837노트

반응식

HRID 404837 반응식
[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[C@H:21]([NH:26][S@@](C(C)(C)C)=O)[C:22]([CH3:25])([CH3:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.Cl.O1CCOCC1>C1COCC1>[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[C@H:21]([NH2:26])[C:22]([CH3:24])([CH3:23])[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 86693889(R)-N-((R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropyl)-2-methylpropane-2-sulfinamide

생성물 1

HCID 86693890HCID 86693890, 화합물수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-N-((R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropyl)-2-methylpropane-2-sulfinamide (53 mg, 0.111 mmol) in THF (200 μL) was added MeOH (55.6 μL) and 4 M HCl in dioxane (55.6 μL, 0.222 mmol). The reaction mixture was stirred at room temperature for 1 h. After quenched with saturated Na2CO3 solution and diluted with EtOAc, the reaction mixture was stirred for 15 min and extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude (R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropan-1-amine was obtained in 99% yield (41 mg), which was used for the next step without further purification (a major side product, methyl 2-methylpropane-2-sulfinate, was completely removed under high vacuum). 1H NMR (CDCl3, 400 MHz): δ 7.96 (1H, m), 7.35-7.29 (2H, m), 7.28-7.22 (3H, m), 7.08 (1H, m), 7.0 (1H, m), 4.18 (2H, m), 3.8 (1H, s), 1.73 (2H, bs), 1.02 (9H, s). LC/MS (uplc): MH+ 356.2, 1.08 min.

후처리

  1. customAfter quenched with saturated Na2CO3 solution
  2. additiondiluted with EtOAc
  3. stirringthe reaction mixture was stirred for 15 min
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b4f28887c4734b2e986db1a1613bc934
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748626B2

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