Ammonia → 6-{2-{[4-(2-Dimethylaminoethoxy)-3-fluorobenzyl]isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950358

반응식

HRID 1950358 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[F:9][C:10]1[CH:11]=[C:12]([CH:44]=[CH:45][C:46]=1[OH:47])[C:13]([N:15]([CH:41]([CH3:43])[CH3:42])[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH:24]1[CH2:33][CH2:32][C:31]2[CH:30]=[C:29]([O:34]C(=O)C(C)(C)C)[CH:28]=[CH:27][C:26]=2[CH2:25]1)=O.Cl[CH2:49][C:50]([N:52]([CH3:54])[CH3:53])=O.[Cl-].[Al+3].[H-].[Al+3].[Li+].N>O1CCCC1>[CH3:53][N:52]([CH3:54])[CH2:50][CH2:49][O:47][C:46]1[CH:45]=[CH:44][C:12]([CH2:13][N:15]([CH:41]([CH3:42])[CH3:43])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[CH:24]2[CH2:33][CH2:32][C:31]3[CH:30]=[C:29]([OH:34])[CH:28]=[CH:27][C:26]=3[CH2:25]2)=[CH:11][C:10]=1[F:9]

참가 물질

8

반응물 6

HCID 222AmmoniaHCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 57934527Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 131727732Lithium aluminum hydride-aluminum chloride

생성물 1

HCID 579338286-{2-{[4-(2-Dimethylaminoethoxy)-3-fluorobenzyl]isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol수율 38.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To cesium carbonate (36 mg) and potassium iodide (5.0 mg) were sequentially added a solution of pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg) in tetrahydrofuran (0.8 ml) and a solution of 2-chloro-N,N-dimethylacetamide (11 mg) in tetrahydrofuran (0.2 ml), and the solution was stirred for 1.5 hours at 60° C. The reaction solution was let to cool, then lithium aluminum hydride-aluminum chloride (1.0 M solution in tetrahydrofuran) (0.57 ml) was added dropwise thereto followed by stirring for 1 hour at room temperature. Tetrahydrofuran and ammonia solution were sequentially added thereto, the solution was filtered through celite pad and concentrated under a nitrogen stream; purified from a solution of the resulting residue in N,N-dimethylformamide by LC-MS, the title compound (9.1 mg) was obtained.

후처리

  1. temperatureto cool
  2. filtrationthe solution was filtered through celite pad
  3. concentrationconcentrated under a nitrogen stream
  4. custompurified from a solution of the resulting residue in N,N-dimethylformamide by LC-MS

출처 및 근거

ORD 기록
ord-06d264ce033f42e49e6f1a1f559a0349
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399520B2

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