Diisopropylethylamine → (+/-)-1-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-6-oxo-piperazine-2-carboxylic acid methyl ester

HRID 1432942노트

반응식

HRID 1432942 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][NH:9][CH2:8][C:7](=[O:11])[N:6]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([N:21]=[C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:14]=1)=[O:4].CCN(C(C)C)C(C)C.[Cl:44][C:45]1[CH:46]=[CH:47][C:48]2[CH:52]=[C:51]([S:53](Cl)(=[O:55])=[O:54])[S:50][C:49]=2[CH:57]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][N:9]([S:53]([C:51]2[S:50][C:49]3[CH:57]=[C:45]([Cl:44])[CH:46]=[CH:47][C:48]=3[CH:52]=2)(=[O:55])=[O:54])[CH2:8][C:7](=[O:11])[N:6]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([N:21]=[C:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]=1)=[O:4]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 54153171(+/-)-1-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-6-oxo-piperazine-2-carboxylic acid methyl ester

생성물 1

HCID 54128933(+/-)-1-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-6-oxo-piperazine-2-carboxylic acid methyl ester수율 73.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A solution containing (±)-1-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-6-oxo-piperazine-2-carboxylic acid methyl ester (55 mg, 0.12 mmol) in CH2Cl2 (1 mL) is cooled to 0° C. DIPEA (24 mg, 0.18 mmol) is then added followed by the addition of 6-chloro-benzo[b]thiophene-2-sulfonyl chloride (32 mg, 0.12 mmol), EXAMPLE 1. The reaction mixture is warmed to ambient temperature. After 16 h, the reaction mixture is absorbed directly onto silica gel and chromatographed (CH2Cl2 to 2% MeOH/CH2Cl2) to provide 60 mg (73%) of the title compound. 1H NMR (300 MHz, CDCl3) δ2.77 (dd, J=12.3, 3.4 Hz, 1H), 3.50-3.72 (m, 3H), 3.79 (s, 3H), 4.15 (dd, J=12.3, 1.4 Hz, 1H), 4.24 (d, J=16.9 Hz, 1H), 5.41 (d, J=15.3 Hz, 1H), 6.50 (s, 1H), 6.76 (dd, J=7.9, 1.4 Hz, 1H), 7.11-7.86 (m, 15H) ppm; MS (ISP loop): m/z 683 (M+H).

후처리

  1. temperatureThe reaction mixture is warmed to ambient temperature
  2. customthe reaction mixture is absorbed directly onto silica gel
  3. customchromatographed (CH2Cl2 to 2% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-e9f546057c7043dd956fb42a25d02bef
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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