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Diisopropylethylamine → (R)-4-(7-chloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidin-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-difluoromethoxy-3-fluoro-benzylamide

HRID 908621
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HRID 908621 반응식
[F:1][CH:2]([F:35])[O:3][C:4]1[CH:33]=[CH:32][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][NH:16][CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:6][C:5]=1[F:34].C(N(CC)C(C)C)(C)C.Cl[C:46]1[S:47][C:48]2[C:53]([Cl:54])=[N:52][C:51]([C:55]([F:58])([F:57])[F:56])=[N:50][C:49]=2[N:59]=1>C(Cl)(Cl)Cl>[F:35][CH:2]([F:1])[O:3][C:4]1[CH:33]=[CH:32][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:46]3[S:47][C:48]4[C:53]([Cl:54])=[N:52][C:51]([C:55]([F:58])([F:57])[F:56])=[N:50][C:49]=4[N:59]=3)[CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]([F:29])([F:31])[F:30])=[CH:25][CH:26]=2)(=[O:20])=[O:19])=[O:11])=[CH:6][C:5]=1[F:34]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 597038262,7-Dichloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidineHCID 59703843(R)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-difluoromethoxy-3-fluoro-benzylamide

생성물 1

HCID 59703768(R)-4-(7-chloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidin-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-difluoromethoxy-3-fluoro-benzylamide수율 79%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of the compound (796 mg) obtained in Step 5 in chloroform (8 ml) were successively added, with stirring under ice-cooling, N,N-diisopropylethylamine (234 mg) and 2,7-dichloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidine (414 mg). After stirring at room temperature for 1 hr, the mixture was partitioned by adding chloroform and water. The aqueous layer was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=6:1-1:2) to give the title compound (912 mg).

후처리

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for 1 hr
  3. customthe mixture was partitioned
  4. additionby adding chloroform and water
  5. extractionThe aqueous layer was extracted with chloroform
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=6:1-1:2)

출처 및 근거

ORD 기록
ord-4229400c0e2044e4adc9cb961e34caba
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017612B2

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