Triethylamine → 1-(3-Fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzoyl)azetidin-3-ol

HRID 1964572노트

반응식

HRID 1964572 반응식
[F:1][C:2]1[CH:30]=[C:29]([C:31]([N:33]2[CH2:36][CH:35]([O:37]C3CCCCO3)[CH2:34]2)=[O:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:17]2[NH:21][C:20]([C:22]3[S:23][CH:24]=[CH:25][N:26]=3)=[CH:19][CH:18]=2)[CH:8]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:10]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(N(CC)CC)C>CO>[F:1][C:2]1[CH:30]=[C:29]([CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:17]2[NH:21][C:20]([C:22]3[S:23][CH:24]=[CH:25][N:26]=3)=[CH:19][CH:18]=2)[CH:8]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:10]=1)[C:31]([N:33]1[CH2:34][CH:35]([OH:37])[CH2:36]1)=[O:32]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 666808962-(5-{3-(2-Fluoro-4-{[3-(tetrahydro-2H-pyran-2-yloxy)azetidin-1-yl]carbonyl}phenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrol-2-yl)-1,3-thiazole

생성물 1

HCID 580655011-(3-Fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzoyl)azetidin-3-ol수율 65.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

2-(5-{3-(2-Fluoro-4-{[3-(tetrahydro-2H-pyran-2-yloxy)azetidin-1-yl]carbonyl}phenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrol-2-yl)-1,3-thiazole (110 mg, 0.181 mmol) synthesized in Example (42b) was dissolved in methanol (10 mL), and 10-camphorsulfonic acid (20 mg, 0.086 mmol) was added, followed by stirring at room temperature overnight under nitrogen atmosphere. To the reaction solution, triethylamine (0.1 mL) was added, and the solvent was distilled off under reduced pressure. The resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=90%-100%) to afford the desired compound (62 mg, yield 65%) as a yellow solid.

후처리

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resulting residue was purified
  3. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=90%-100%)

출처 및 근거

ORD 기록
ord-b93fd317c0c840e589c0326a47214048
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415359B2

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