1,2-Dichloroethane → HCID 58754890, 화합물

HRID 1619210노트

반응식

HRID 1619210 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.BrC1SC=CN=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([C:31](O)=[O:32])=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.O.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([N:9]3[CH2:8][CH2:7][N:6]([C:2]4[S:1][CH:5]=[CH:4][N:3]=4)[CH2:11][CH2:10]3)=[O:32])=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 764302-BromothiazoleHCID 9118061-(Thiazol-2-yl)piperazineHCID 27574173'-Chloro[1,1'-biphenyl]-4-carboxylic acid

생성물 1

HCID 58754890HCID 58754890, 화합물수율 64%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(thiazol-2-yl)piperazine (ca. 0.915 mmol, prepared from 150 mg 2-bromothiazole according to the methods described in Astles et al., J. Med. Chem., 39: 1423-1432 (1996)), 3′-chloro-biphenyl-4-carboxylic acid (212.9 mg, 0.915 mmol) in CH2Cl2 (4 ml), was added EDC (209.7 mg, 1.098 mmol) and HOBt (148.2 mg, 1.098 mmol). After being stirred overnight, the mixture was treated with EtOAc (50 ml) and water (15 ml). The organic phase was washed with brine (5 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (20% acetone/hexanes) to give the title compound (225 mg, 64% for two steps) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 7.64-7.23 (m, 9H), 6.65 (t, J=3.6 Hz, 1H), 4.92 (m, br, 2H), 3.57 (m, br, 6H), 3.68 (m, 2H), 2.14 (m, 2H), 1.83 (m, 2H); MS calc'd for C20H19ClN3OS [M+H]+: 384; Found: 384.

후처리

  1. washThe organic phase was washed with brine (5 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto furnish the crude product
  6. customThis material was purified by column chromatography (20% acetone/hexanes)

출처 및 근거

ORD 기록
ord-edd1667b70a44c6496ea02cab0e4021a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772291B2

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