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

HRID 908648
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HRID 908648 반응식
[F:1][C:2]([F:33])([F:32])[O:3][C:4]1[CH:31]=[CH:30][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]([CH:27]3[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:6][CH:5]=1.Cl[C:35]1[S:36][C:37]2[C:42]([Cl:43])=[N:41][C:40]([CH:44]3[CH2:46][CH2:45]3)=[N:39][C:38]=2[N:47]=1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[F:33][C:2]([F:1])([F:32])[O:3][C:4]1[CH:31]=[CH:30][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:35]3[S:36][C:37]4[C:42]([Cl:43])=[N:41][C:40]([CH:44]5[CH2:45][CH2:46]5)=[N:39][C:38]=4[N:47]=3)[CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]3[CH2:28][CH2:29]3)=[CH:23][CH:22]=2)(=[O:19])=[O:20])=[O:11])=[CH:6][CH:5]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 597037622,7-Dichloro-5-cyclopropyl-thiazolo[4,5-d]pyrimidineHCID 59703776(R)-1-(4-cyclopropyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

생성물 1

HCID 59703855(R)-4-(7-chloro-5-cyclopropyl-thiazolo[4,5-d]pyrimidin-2-yl)-1-(4-cyclopropyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide수율 96.6%

시약·촉매·용매

2
HCID 6212Chloroform용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of (R)-1-(4-cyclopropyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide (39 mg) obtained in Example 1100, Step 4 and 2,7-dichloro-5-cyclopropyl-thiazolo [4,5-d]pyrimidine (20 mg) in chloroform (1.0 ml) was added N,N-diisopropylethylamine (20 μl) at room temperature. After stirring overnight at room temperature, the reaction mixture was diluted with ethyl acetate, and the mixture was partitioned by adding water. The organic layer was dried over anhydrous sodium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) to give the title compound (54 mg).

후처리

  1. customthe mixture was partitioned
  2. additionby adding water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)

출처 및 근거

ORD 기록
ord-a9709734a0da4473aac388ad367aee99
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017612B2

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