Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)pyridin-3-yl)benzo[d]thiazol-6-yl)ethanol

HRID 879307노트

반응식

HRID 879307 반응식
C([O:7][CH2:8][C@@H:9]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:10]1[C:34]([CH3:35])=[CH:33][C:13]2[N:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[N:28]([CH3:32])[N:27]=[CH:26]5)[CH:22]=3)[S:16][C:12]=2[C:11]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)(=O)C(C)(C)C.C1COCC1.CO.[OH-].[Na+]>C(OCC)(=O)C>[C:44]([O:43][C@@H:9]([C:10]1[C:34]([CH3:35])=[CH:33][C:13]2[N:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[N:28]([CH3:32])[N:27]=[CH:26]5)[CH:22]=3)[S:16][C:12]=2[C:11]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[CH2:8][OH:7])([CH3:47])([CH3:45])[CH3:46]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 86699827(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)pyridin-3-yl)benzo[d]thiazol-6-yl)ethyl pivalate

생성물 1

HCID 86699828(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)pyridin-3-yl)benzo[d]thiazol-6-yl)ethanol

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
55 °C

실험 절차

To a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)pyridin-3-yl)benzo[d]thiazol-6-yl)ethyl pivalate from above reaction was added THF:MeOH (1:1, 2 mL) and 2M NaOH (0.5 mL) were added and reaction mixture was heated at 55° C. for 3 h. Reaction mixture was cooled to rt, diluted with ethyl acetate and washed with saturated ammonium chloride solution. The organic layer was dried (MgSO4), filtered, concentrated and purified by CombiFlash (EtOAC/Hex) to give (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)pyridin-3-yl)benzo[d]thiazol-6-yl)ethanol (15 mg). LCMS-ESI+: calc'd for C33H32ClN4O2S: 583.2 (M+H+); found: 583.3 (M+H+).

후처리

  1. additionwere added
  2. customreaction mixture
  3. customReaction mixture
  4. temperaturewas cooled to rt
  5. washwashed with saturated ammonium chloride solution
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by CombiFlash (EtOAC/Hex)

출처 및 근거

ORD 기록
ord-2209d6a4be3e4df094c9fa1ee452079f
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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